Microbiocidal picolinamide derivatives

ABSTRACT

Compounds of the formula (I) wherein the substituents are as defined in claim  1 , useful as pesticides, and especially fungicides.

The present invention relates to microbiocidal picolinamide derivatives,e.g., as active ingredients, which have microbiocidal activity, inparticular fungicidal activity. The invention also relates to thepreparation of these picolinamide derivatives, to agrochemicalcompositions which comprise at least one of the picolinamide derivativesand to uses of the picolinamide derivatives or compositions thereof inagriculture or horticulture for controlling or preventing theinfestation of plants, harvested food crops, seeds or non-livingmaterials by phytopathogenic microorganisms, preferably fungi.

Picolinamide compounds as fungicidal agents are described in WO2016/109288, WO 2016/109289, WO 2016/109300, WO 2016/109301, WO2016/109302 and WO 2016/109303.

According to the present invention, there is provided compound offormula (I):

-   -   wherein,    -   R¹ is C₁-C₁₂alkyl or C₁-C₆haloalkyl;    -   R² is hydroxy, C₂-C₆acyloxy, C₂-C₆haloacyloxy,        C₁-C₆alkoxyC₁-C₆alkoxy, C₁-C₆haloalkoxyC₁-C₆alkoxy,        C₁-C₆alkoxyC₁-C₆haloalkoxy, C₂-C₆acyloxyC₁-C₆alkoxy,        C₂-C₆haloacyloxyC₁-C₆alkoxy or C₂-C₆acyloxyC₁-C₆haloalkoxy;    -   R³ is hydrogen, C₁-C₆alkyl, C₁-C₆alkoxy or C₃-C₈cycloalkyl;    -   R⁴ and R⁵ are independently C₁-C₁₂alkyl, C₃-C₈cycloalkyl,        C₁-C₆haloalkyl, C₁-C₆alkoxyC₁-C₆alkyl or C₃-C₈halocycloalkyl;    -   R⁶ and R⁷ are independently C₁-C₆alkyl or C₃-C₈cycloalkyl; or    -   R⁶ and R⁷ together with the carbon atom to which they are        attached form a C₃-C₈cycloalkyl ring which is optionally        substituted by 1, 2 or 3 substituents, which may be the same or        different, selected from R⁹, or is optionally substituted by a        single substituent which is R¹⁰, or is optionally substituted by        1 or 2 substituents, which may be the same or different,        selected from R⁹ and a single substituent which is R¹⁰;    -   R⁸ is phenyl, phenoxy, naphthyl, naphthyloxy, heteroaryl or        heteroaryloxy, wherein the heteroaryl moiety is a 5- or        6-membered aromatic ring which comprises 1, 2, 3 or 4        heteroatoms individually selected from N, O and S, heterodiaryl        or heterodiaryloxy, wherein the heterodiaryl moiety is a 9- or        10-membered bicyclic aromatic system which comprises 1, 2, 3 or        4 heteroatoms individually selected from N, O and S, wherein        each phenyl, naphthyl, heteroaryl or heterodiaryl is optionally        substituted by 1, 2 or 3 substituents, which may be the same or        different, selected from R⁹;    -   R⁹ is halogen, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,        C₁-C₄haloalkoxy; and    -   R¹⁰ is phenyl or cyclopropyl each optionally substituted by 1, 2        or 3 substituents, which may be the same or different, selected        from fluoro, chloro, bromo, cyano, methyl, ethyl,        difluoromethyl, trifluoromethyl, methoxy, ethoxy,        difluoromethoxy, trifluoromethoxy; or    -   a salt or an N-oxide thereof.

Surprisingly, it has been found that the novel compounds of formula (I)have, for practical purposes, a very advantageous level of biologicalactivity for protecting plants against diseases that are caused byfungi.

According to a second aspect of the invention, there is provided anagrochemical composition comprising a fungicidally effective amount of acompound of formula (I) according to the present invention. Such anagricultural composition may further comprise at least one additionalactive ingredient and/or an agrochemically-acceptable diluent orcarrier.

According to a third aspect of the invention, there is provided a methodof controlling or preventing infestation of useful plants byphytopathogenic microorganisms, wherein a fungicidally effective amountof a compound of formula (I), or a composition comprising this compoundas active ingredient, is applied to the plants, to parts thereof or thelocus thereof.

According to a fourth aspect of the invention, there is provided the useof a compound of formula (I) as a fungicide. According to thisparticular aspect of the invention, the use may exclude methods for thetreatment of the human or animal body by surgery or therapy.

Where substituents are indicated as being “optionally substituted”, thismeans that they may or may not carry one or more identical or differentsubstituents, e.g., one, two or three, etc, R⁹ or R¹⁰ substituents. Forexample, C₁-C₆alkyl substituted by 1, 2 or 3 halogens, may include, butnot be limited to, —CH₂Cl, —CHCl₂, —CCl₃, —CH₂F, —CHF₂, —CF₃, —CH₂CF₃ or—CF₂CH₃ groups. As another example, C₁-C₆alkoxy substituted by 1, 2 or 3halogens, may include, but not be limited to, CH₂ClO—, CHCl₂O—, CCl₃O—,CH₂FO—, CHF₂O—, CF₃O—, CF₃CH₂O— or CH₃CF₂O— groups.

As used herein, the term “hydroxyl” or “hydroxy” means a —OH group.

As used herein, the term “cyano” means a —CN group.

As used herein, the term “halogen” refers to fluorine (fluoro), chlorine(chloro), bromine (bromo) or iodine (iodo).

As used herein, the term “C₁-C₆alkyl” refers to a straight or branchedhydrocarbon chain radical consisting solely of carbon and hydrogenatoms, containing no unsaturation, having from one to six carbon atoms,and which is attached to the rest of the molecule by a single bond. Theterms “C₁-C₁₂alkyl” and “C₁-C₄alkyl” are to be construed accordingly.Examples of C₁-C₆alkyl include, but are not limited to, methyl, ethyl,n-propyl, n-butyl, n-pentyl, n-hexyl and the isomers thereof, forexample, iso-propyl, iso-butyl, sec-butyl, tert-butyl or iso-amyl. A“C₁-C₆alkylene” group refers to the corresponding definition ofC₁-C₆alkyl, except that such radical is attached to the rest of themolecule by two single bonds. The term “C₁-C₂alkylene” is to beconstrued accordingly. Examples of C₁-C₆alkylene, include, but are notlimited to, —CH₂—, —CH₂CH₂— and —(CH₂)₃—.

As used herein, the term “C₃-C₈cycloalkyl” refers to a radical which isa monocyclic saturated ring system and which contains 3 to 8 carbonatoms. The term “C₃-C₆cycloalkyl” is to be construed accordingly.Examples of C₃-C₈cycloalkyl include, but are not limited to,cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl andcyclooctyl.

As used herein, the term “C₃-C₈halocycloalkyl” refers to aC₃-C₈cycloalkyl radical as generally defined above substituted by one ormore of the same or different halogen atoms. The term“C₃-C₆halocycloalkyl” is to be construed accordingly.

As used herein, the term “C₁-C₆alkoxy” refers to a radical of theformula —OR_(a) where R_(a) is a C₁-C₆alkyl radical as generally definedabove. The term “C₁-C₄alkoxy” is to be construed accordingly. Examplesof C₁-C₆alkoxy include, but are not limited to, methoxy, ethoxy,1-methylethoxy (iso-propoxy), propoxy, butoxy, 1-methylpropoxy and2-methylpropoxy.

As used herein, the term “C₁-C₆haloalkyl” refers a C₁-C₆alkyl radical asgenerally defined above substituted by one or more of the same ordifferent halogen atoms. The terms “C₁-C₄haloalkyl” and “C₁-C₂haloalkyl”are to be construed accordingly. Examples of C₁-C₆haloalkyl include, butare not limited to trifluoromethyl.

As used herein, the term “C₁-C₆alkoxyC₁-C₆alkoxy” refers to a radical ofthe formula R_(b)O—R_(a)O— where R_(b) is a C₁-C₆alkyl radical asgenerally defined above, and R_(a) is a C₁-C₆alkylene radical asgenerally defined above. Examples of C₁-C₆alkoxyC₁-C₆alkoxy include, butare not limited to, methoxymethoxy, ethoxymethoxy and methoxyethoxy.

As used herein, the term “C₁-C₆haloalkoxyC₁-C₆alkoxy” refers to aradical of the formula R_(b)O—R_(a)O—, where R_(a) is a C₁-C₆alkyleneradical as generally defined above and R_(b) is a C₁-C₆alkyl radical asgenerally defined above substituted by one or more of the same ordifferent halogen atoms. Examples of C₁-C₆haloalkoxyC₁-C₆alkoxy groupsinclude, but not limited to trifluoromethoxymethoxy.

As used herein, the term “C₁-C₆alkoxyC₁-C₆haloalkoxy” refers to aradical of the formula R_(a)O—R_(b)O—, where R_(a) is a C₁-C₆alkylradical as generally defined above and R_(b) is a C₁-C₆alkylene radicalas generally defined above substituted by one or more of the same ordifferent halogen atoms. Examples of C₁-C₆alkoxyC₁-C₆haloalkoxy groupsinclude, but not limited to methoxydifluoromethoxy.

As used herein, the term “C₂-C₆acyl” refers to a radical R_(a)C(═O)—,where R_(a) is a C₁-C₅alkyl radical as generally defined above. Acylgroups include, but are not limited to, acetyl and propanoyl.

As used herein, the term “C₂-C₆acyloxy” refers to a radical of theformula —OR_(a) where R_(a) is a C₂-C₆acyl as generally defined above.C₂-C₆acyloxy groups include, but are not limited to, acetoxy,propanoyloxy, isopropanoyloxy, butanoyloxy, and cyclopropanoyloxy.

As used herein, the term “C₂-C₆haloacyloxy” refers to a radical of theformula R_(a)C(═O)O—, where R_(a) is C₁-C₅alkyl radical as generallydefined above substituted by one or more of the same or differenthalogen atoms. C₂-C₆haloacyloxy groups include, but are not limited totrifluoroacetoxy.

As used herein, the term “C₂-C₆acyloxyC₁-C₆alkoxy” refers to a radicalof the formula R_(a)C(═O)OR_(b)O— where R_(a) is a C₁-C₅alkyl radical asgenerally defined above and where R_(b) is a C₁-C₆alkylene radical asgenerally defined above.

As used herein, the term “C₂-C₆haloacyloxyC₁-C₆alkoxy” refers to aradical of the formula R_(a)C(═O)OR_(b)O— where R_(a) is a C₁-C₅alkylradical as generally defined above substituted by one or more of thesame or different halogen atoms, and R_(b) is a C₁-C₆alkylene radical asgenerally defined above.

As used herein, the term “C₂-C₆acyloxyC₁-C₆haloalkoxy” refers to aradical of the formula R_(a)C(═O)OR_(b)O— where R_(a) is a C₁-C₅alkylradical as generally defined above, and R_(b) is a C₁-C₆alkylene radicalas generally defined above substituted by one or more of the same ordifferent halogen atoms.

As used herein, the term “heteroaryl” refers to a 5- or 6-memberedaromatic monocyclic ring radical which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S. Examples ofheteroaryl include, but are not limited to, furanyl, pyrrolyl, thienyl,pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl,triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl or pyridyl.

As used herein, the term “heteroaryloxy” refers to a radical of theformula —OR_(a) where R_(a) is a heteroaryl radical as generally definedabove. Examples of heteroaryloxy include, but are not limited to,pyridyloxy and thienyloxy.

As used herein, the term “heterodiaryl” refers to a 9- or 10-memberedbicyclic aromatic system which comprises 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S. Examples of heterodiaryl include,but are not limited to quinolinyl and indolinyl.

As used herein, the term “heterodiaryloxy” refers to a radical of theformula —OR_(a) where R_(a) is a heterodiaryl radical as generallydefined above.

The presence of one or more possible asymmetric carbon atoms in acompound of formula (I) means that the compounds may occur in opticallyisomeric forms, i.e., enantiomeric or diastereomeric forms. Also,atropisomers may occur as a result of restricted rotation about a singlebond. Formula (I) is intended to include all those possible isomericforms and mixtures thereof. The present invention includes all thosepossible isomeric forms and mixtures thereof for a compound of formula(I). Likewise, formula (I) is intended to include all possibletautomers. The present invention includes all possible tautomeric formsfor a compound of formula (I).

In each case, the compounds of formula (I) according to the inventionare in free form, in oxidized form as an N-oxide, or in salt form, e.g.,an agronomically usable salt form.

N-oxides are oxidized forms of tertiary amines or oxidized forms ofnitrogen-containing heteroaromatic compounds. They are described forinstance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra,CRC Press, Boca Raton (1991).

The following list provides definitions, including preferreddefinitions, for substituents R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ andR¹⁰, with reference to compounds of formula (I). For any one of thesesubstituents, any of the definitions given below may be combined withany definition of any other substituent given below or elsewhere in thisdocument.

R¹ is C₁-C₁₂alkyl or C₁-C₆haloalkyl. Preferably, R¹ is C₁-C₆alkyl orC₁-C₄haloalkyl, more preferably, C₁-C₄alkyl or C₁-C₂haloalkyl, and evenmore preferably, C₁-C₃alkyl (including methyl or ethyl), difluoromethylor trifluoromethyl. Particularly preferably, R¹ is methyl or ethyl, andin particular methyl.

R² is hydroxy, C₂-C₆acyloxy, C₂-C₆haloacyloxy, C₁-C₆alkoxyC₁-C₆alkoxy,C₁-C₆haloalkoxyC₁-C₆alkoxy, C₁-C₆alkoxyC₁-C₆haloalkoxy,C₂-C₆acyloxyC₁-C₆alkoxy, C₂-C₆haloacyloxyC₁-C₆alkoxy orC₂-C₆acyloxyC₁-C₆haloalkoxy. Preferably, R² is hydroxy, C₂-C₄acyloxy,C₂-C₄haloacyloxy, C₁-C₄alkoxyC₁-C₄alkoxy, C₁-C₄haloalkoxyC₁-C₄alkoxy,C₁-C₄alkoxyC₁-C₄haloalkoxy, C₂-C₄acyloxyC₁-C₄alkoxy,C₂-C₄haloacyloxyC₁-C₄alkoxy or C₂-C₄acyloxyC₁-C₄haloalkoxy. Morepreferably, R² is hydroxy, acetoxy, propanoyloxy, acetoxymethoxy,propanoyloxymethoxy, 2-methyl-propanoyloxymethoxy. Particularlypreferably, R² is hydroxy.

R³ is hydrogen, C₁-C₆alkyl, C₁-C₆alkoxy or C₃-C₈cycloalkyl. Preferably,R³ is hydrogen, C₁-C₄alkyl, C₁-C₄alkoxy or C₃-C₆cycloalkyl, and morepreferably, hydrogen, methyl, ethyl, methoxy, cyclopropyl. Morepreferably, R³ is hydrogen.

R⁴ and R⁵ are independently selected from C₁-C₁₂alkyl, C₃-C₈cycloalkyl,C₁-C₆haloalkyl, C₁-C₆alkoxyC₁-C₆alkyl and C₃-C₈halocycloalkyl.Preferably, R⁴ and R⁵ are independently selected from C₁-C₄alkyl,C₃-C₆cycloalkyl, C₁-C₄haloalkyl, C₁-C₄alkoxyC₁-C₄alkyl andC₃-C₆halocycloalkyl. More preferably, R⁴ and R⁵ are independentlyselected from methyl, ethyl, cyclopropyl, difluoromethyl,trifluoromethyl, methoxymethyl, ethoxymethyl, ethoxymethyl andfluorocyclopropyl. Even more preferably, R⁴ is methyl or ethyl and R⁵ ismethyl or ethyl (including R⁴ is methyl and R⁵ is ethyl, or R⁴ is ethyland R⁵ is methyl), and in particular, R⁴ and R⁵ are methyl.

R⁶ and R⁷ are independently selected from C₁-C₆alkyl or C₃-C₈cycloalkyl.Preferably, R⁶ and R⁷ are independently selected from C₁-C₄alkyl orC₃-C₆cycloalkyl. More preferably, R⁶ and R⁷ are independently selectedfrom methyl, ethyl or cyclopropyl. More preferably, R⁶ and R⁷ aremethyl.

Otherwise, R⁶ and R⁷ together with the carbon atom to which they areattached may form a C₃-C₈cycloalkyl ring, preferably a C₃-C₆cycloalkylring (i.e., cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl), andmore preferably a cyclopropyl ring, which is optionally substituted by1, 2 or 3 substituents, which may be the same or different, selectedfrom R⁹, or is optionally substituted by a single substituent which isR¹⁰, or is optionally substituted by 1 or 2 substituents, which may bethe same or different, selected from R⁹ and a single substituent whichis R¹⁰.

R⁸ is phenyl, phenoxy, naphthyl, naphthyloxy, heteroaryl orheteroaryloxy, wherein the heteroaryl moiety is a 5- or 6-memberedaromatic ring which comprises 1, 2, 3 or 4 heteroatoms individuallyselected from N, O and S, heterodiaryl or heterodiaryloxy, wherein theheterodiaryl moiety is a 9- or 10-membered bicyclic aromatic systemwhich comprises 1, 2, 3 or 4 heteroatoms individually selected from N, Oand S, wherein each phenyl, naphthyl, heteroaryl or heterodiaryl isoptionally substituted by 1, 2 or 3 substituents, which may be the sameor different, selected from R⁹.

Preferably, R⁸ is phenyl, naphthyl, furyl, benzofuryl, thienyl,benzothienyl, pyrrolyl, indolyl, pyrazolyl, indazolyl, imidazolyl,benzimidazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl,pyridyl, quinolinyl, isoquinolinyl, pyridazinyl, cinnolinyl,pyrimidinyl, quinazolinyl, pyrazinyl, phenoxy, naphthyloxy, pyridyloxyor quinolinyloxy. More preferably, R⁸ is phenyl, naphthyl, thienyl,indolyl, pyridyl, quinolinyl, pyridazinyl, pyrimidinyl, pyrazinyl,phenoxy, pyridyloxy or quinolinyloxy. Still more preferably, R⁸ isphenyl, naphthyl (1-naphthyl, 2-naphthyl), thienyl (2-thienyl,3-thienyl), pyridyl (2-pyridyl, 3-pyridyl, 4-pyridyl), quinolinyl(including 2-quinolinyl, 3-quinolinyl), phenoxy or pyridyloxy (including2-pyridyloxy, 3-pyridyloxy). Even more preferably, R⁸ is phenyl, thienyl(2-thienyl, 3-thienyl), pyridyl (2-pyridyl, 3-pyridyl, 4-pyridyl),phenoxy or pyridyloxy (2-pyridyloxy, 3-pyridyloxy), and in particularphenyl.

For R⁸, heteroaryl and heterodiaryl substituents may be bound to therest of the molecule by a carbon atom or a heteroatom.

When R⁸ is substituted, it may be substituted by 1 or 2 substituents,which may be the same or different, selected from R⁹. Otherwise, when R⁸is substituted, it may be substituted by a single substituent selectedfrom R⁹.

R⁹ is halogen, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy. Preferably, R⁹ is fluoro, chloro, bromo, cyano, methyl,ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy ortrifluoromethoxy. More preferably, R⁹ is fluoro, chloro, cyano, methyl,ethyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy ortrifluoromethoxy. In one set of embodiments, R⁹ is fluoro, chloro,bromo, trifluoromethyl, ethoxy or trifluoromethoxy.

R¹⁰ is phenyl or cyclopropyl each optionally substituted by 1, 2 or 3substituents, which may be the same or different, selected from fluoro,chloro, bromo, cyano, methyl, ethyl, difluoromethyl, trifluoromethyl,methoxy, ethoxy, difluoromethoxy, trifluoromethoxy. When R¹⁰ issubstituted, it may be substituted by 1 or 2 substituents, which may bethe same or different. Otherwise, when R¹⁰ is substituted, it may besubstituted by a single substituent, preferably fluoro.

In a compound of formula (I) according to the present invention,preferably:

-   -   R¹ is methyl or ethyl;    -   R² is hydroxy, acetoxy, propanoyloxy, acetoxymethoxy,        propanoyloxymethoxy or 2-methyl-propanoyloxymethoxy;    -   R³ is hydrogen, methyl, ethyl, methoxy or cyclopropyl;    -   R⁴ is methyl or ethyl and R⁵ is methyl or ethyl;    -   R⁶ and R⁷ are independently selected from methyl, ethyl or        cyclopropyl, or    -   R⁶ and R⁷ together with the carbon atom to which they are        attached form a C₃-C₆cycloalkyl ring which is optionally        substituted by by 1 or 2 substituents, which may be the same or        different, selected from R⁹, or is optionally substituted by a        single substituent which is R¹⁰;    -   R⁸ is phenyl, naphthyl, thienyl, indolyl, pyridyl, quinolinyl,        pyridazinyl, pyrimidinyl, pyrazinyl, phenoxy, pyridyloxy or        quinolinyloxy optionally substituted by 1 or 2 substituents,        which may be the same or different, selected from R⁹;    -   R⁹ is fluoro, chloro, cyano, methyl, ethyl, difluoromethyl,        trifluoromethyl, methoxy, ethoxy or trifluoromethoxy;    -   R¹⁰ is phenyl or cyclopropyl each optionally substituted by 1 or        2 substituents, which may be the same or different, selected        from fluoro, chloro, bromo, cyano, methyl, ethyl,        difluoromethyl, trifluoromethyl, methoxy, ethoxy,        difluoromethoxy, trifluoromethoxy.

More preferably, R¹ is methyl or ethyl;

-   -   R² is hydroxy;    -   R³ is hydrogen;    -   R⁴ is methyl or ethyl and R⁵ is methyl or ethyl;    -   R⁶ and R⁷ are independently selected from methyl, ethyl or        cyclopropyl, or R⁶ and R⁷ together with the carbon atom to which        they are attached form a C₃-C₆cycloalkyl ring which is        optionally substituted by by 1 or 2 substituents, which may be        the same or different, selected from R⁹, or is optionally        substituted by a single substituent which is R¹⁰;    -   R⁸ is phenyl, naphthyl, thienyl, indolyl, pyridyl, quinolinyl,        pyridazinyl, pyrimidinyl, pyrazinyl, phenoxy, pyridyloxy or        quinolinyloxy optionally substituted by 1 or 2 substituents,        which may be the same or different, selected from R⁹;    -   R⁹ is fluoro, chloro, cyano, methyl, ethyl, difluoromethyl,        trifluoromethyl, methoxy, ethoxy or trifluoromethoxy;    -   R¹⁰ is phenyl or cyclopropyl each optionally substituted by 1 or        2 substituents, which may be the same or different, selected        from fluoro, chloro, bromo, cyano, methyl, ethyl,        difluoromethyl, trifluoromethyl, methoxy, ethoxy,        difluoromethoxy, trifluoromethoxy.

Even more preferably, R¹ is methyl;

-   -   R² is hydroxy;    -   R³ is hydrogen;    -   R⁴ and R⁵ are methyl;    -   R⁶ and R⁷ are methyl, or    -   R⁶ and R⁷ together with the carbon atom to which they are        attached form a C₃-C₆cycloalkyl ring which is optionally        substituted by by 1 or 2 substituents, which may be the same or        different, selected from R⁹, or is optionally substituted by a        single substituent which is R¹⁰;    -   R⁸ is phenyl, thienyl, pyridyl, phenoxy or pyridyloxy optionally        substituted by 1 or 2 substituents, which may be the same or        different, selected from R⁹;    -   R⁹ is fluoro, chloro, cyano, methyl, ethyl, difluoromethyl,        trifluoromethyl, methoxy, ethoxy or trifluoromethoxy;    -   R¹⁰ is phenyl or cyclopropyl each optionally substituted by 1 or        2 substituents, which may be the same or different, selected        from fluoro, chloro, bromo, cyano, methyl, ethyl,        difluoromethyl, trifluoromethyl, methoxy, ethoxy,        difluoromethoxy, trifluoromethoxy.

Still more preferably, R¹ is methyl;

-   -   R² is hydroxy;    -   R³ is hydrogen;    -   R⁴ and R⁵ are methyl;    -   R⁶ and R⁷ are methyl, or    -   R⁶ and R⁷ together with the carbon atom to which they are        attached form a cyclopropyl ring which is optionally substituted        by 1 or 2 substituents, which may be the same or different,        selected from R⁹, or is optionally substituted by a single        substituent which is R¹⁰;    -   R⁸ is phenyl optionally substituted by 1 or 2 substituents,        which may be the same or different, selected from R⁹;    -   R⁹ is fluoro, chloro, cyano, methyl, ethyl, difluoromethyl,        trifluoromethyl, methoxy, ethoxy or trifluoromethoxy;    -   R¹⁰ is phenyl or cyclopropyl each optionally substituted by 1 or        2 substituents, which may be the same or different, selected        from fluoro, chloro, bromo, cyano, methyl, ethyl,        difluoromethyl, trifluoromethyl, methoxy, ethoxy,        difluoromethoxy, trifluoromethoxy.

In a particular set of embodiments according to the invention,

-   -   R¹ is methyl;    -   R² is hydroxy or acetoxy;    -   R³ is hydrogen;    -   R⁴ and R⁵ are methyl;    -   R⁶ and R⁷ are methyl, or    -   R⁶ and R⁷ together with the carbon atom to which they are        attached form a cyclopropyl ring which is optionally substituted        by 1 or 2 substituents, which may be the same or different,        selected from R⁹, or is optionally substituted by a single        substituent which is R¹⁰; or    -   R⁶ and R⁷ together with the carbon atom to which they are        attached form a cyclobutyl, cyclopentyl or cyclohexyl ring;    -   R⁸ is naphthyl, or R⁸ is phenyl optionally substituted by 1 or 2        substituents, which may be the same or different, selected from        R⁹;    -   R⁹ is fluoro, chloro, bromo, trifluoromethyl, ethoxy or        trifluoromethoxy; and    -   R¹⁰ is phenyl or 4-fluorophenyl.

Preferably, the compound according to formula (I) is a compounddescribed in Table 2 (below) and/or is one of the following preferredcompounds.

The compounds of Formula (I) according to the present invention maypossess three chiral centres at carbon atoms A, B and C as outlinedbelow in Formula (A).

Accordingly, as already indicated, the compounds of Formula (I) mayexist in various diastereomeric forms, ie, with (S,S,S)-, (S,S,R)-,(S,R,R)-, (S,R,S)-, (R,R,R)-, (R,R,S)-, (R,S,S)- or(R,S,R)-configurations present at the A, B and C carbons, respectively.In particular, each of these configurations may be evident for compoundsof Formula (I) in relation to the specifc combinations of definitionsfor R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ for each compound described inTable 1 (a compound of Formulae (1.a) to (1.ah)) or a compound ofFormula (I) described in Table 2 (below).

Compounds of the present invention can be made as shown in the followingschemes, in which, unless otherwise stated, the definition of eachvariable is as defined above for a compound of formula (I).

The compounds of formula (I) according to the invention, wherein R¹, R²,R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for formula (I), can beobtained by transformation of a compound of formula (II), wherein R¹ andR² are as defined for formula (I) and R¹¹ is hydroxy or halogen, with acompound of formula (III), wherein R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are asdefined for formula (I), and with a base or a peptide coupling reagent.This is shown in Scheme 1 below.

Alternatively, the compounds of formula (I), wherein R¹, R², R³, R⁴, R⁵,R⁶, R⁷ and R⁸ are as defined for formula (I), can be obtained bytransformation of a compound of formula (IV), wherein R¹, R², R³, and R⁴are as defined for formula (I) and R¹¹ is hydroxy or halogen, with acompound of formula (V), wherein R⁵, R⁶, R⁷ and R⁸ are as defined forformula (I), and with an acid or a base. This is shown in Scheme 2below.

The compounds of formula (III), wherein R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are asdefined for formula (I), can be obtained by transformation of a compoundof formula (VI), wherein R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined forformula (I) and R¹² is C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl, andwith an acid. This is shown in Scheme 3 below.

The compounds of formula (VI), wherein R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are asdefined for formula (I) and R¹² is C₁-C₆alkylcarbonyl orC₁-C₆alkoxycarbonyl, can be obtained by transformation of a compound offormula (VII), wherein R³ and R⁴ are as defined for formula (I), R¹¹ ishydroxy or halogen and R¹² is C₁-C₆alkylcarbonyl or C₁-C₆alkoxycarbonyl,with a compound of formula (V), wherein R⁵, R⁶, R⁷ and R⁸ are as definedfor formula (I), and with an acid or a base. This is shown in Scheme 4below.

The compounds of formula (IV), wherein R¹, R², R³, and R⁴ are as definedfor formula (I) and R¹¹ is hydroxy or halogen, can be obtained bytransformation of a compound of formula (VIII), wherein R¹, R², R³, andR⁴ are as defined for formula (I) and R¹³ is C₁-C₆alkyl, and with a baseor a halogenation agent. This is shown in Scheme 5 below.

The compounds of formula (VIII), wherein R¹, R², R³, and R⁴ are asdefined for formula (I) and R¹³ is C₁-C₆alkyl, can be obtained bytransformation of a compound of formula (II), wherein R¹ and R² are asdefined for formula (I) and R¹¹ is hydroxy or halogen, with a compoundof formula (IX), wherein R³ and R⁴ are as defined for formula (I) andR¹³ is C₁-C₆alkyl, and with a base or a peptide coupling reagent.

This is shown in Scheme 6 below.

The compounds of formula (I-B), wherein R¹, R³, R⁴, R⁵, R⁶, R⁷ and R areas defined for formula (I) and R¹⁴ is C₂-C₆acyloxy, C₂-C₆haloacyloxy,C₁-C₆alkoxyC₁-C₆alkoxy, C₁-C₆haloalkoxyC₁-C₆alkoxy,C₁-C₆alkoxyC₁-C₆haloalkoxy, C₂-C₆acyloxyC₁-C₆alkoxy,C₂-C₆haloacyloxyC₁-C₆alkoxy, or C₂-C₆acyloxyC₁-C₆haloalkoxy, can beobtained by transformation of a compound of formula (I-A), wherein R¹,R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for formula (I), with acompound of formula (X), wherein R¹⁴ is C₂-C₆acyloxy, C₂-C₆haloacyloxy,C₁-C₆alkoxyC₁-C₆alkoxy, C₂-C₆haloalkoxyC₁-C₆alkoxy,C₁-C₆alkoxyC₁-C₆haloalkoxy, C₂-C₆acyloxyC₁-C₆alkoxy,C₂-C₆haloacyloxyC₁-C₆alkoxy, or C₂-C₆acyloxyC₁-C₆haloalkoxy and R¹⁵ ishalogen, and with a base. This is shown in Scheme 7 below.

The compounds of formula (I-A), wherein R¹, R³, R⁴, R⁵, R⁶, R⁷ and R areas defined for formula (I), can be obtained by transformation of acompound of formula (II-A), wherein R¹ is as defined for formula (I) andR¹¹ is hydroxy or halogen, with a compound of formula (III), wherein R³,R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined for formula (I), and with a base ora peptide coupling reagent. This is shown in Scheme 8 below.

Alternatively, the compounds of formula (I-A), wherein R¹, R³, R⁴, R⁵,R⁶, R⁷ and R⁸ are as defined for formula (I), can be obtained bytransformation of a compound of formula (IV-A), wherein R¹, R³, and R⁴are as defined for formula (I) and R¹¹ is hydroxy or halogen, with acompound of formula (V), wherein R⁵, R⁶, R⁷ and R⁸ are as defined forformula (I), and with an acid or a base. This is shown in Scheme 9below.

Alternatively, the compounds of formula (I-B) according to theinvention, wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are as defined forformula (I) and R¹⁴ is C₂-C₆acyloxy, C₂-C₆haloacyloxy,C₁-C₆alkoxyC₁-C₆alkoxy, C₁-C₆haloalkoxyC₁-C₆alkoxy,C₁-C₆alkoxyC₁-C₆haloalkoxy, C₂-C₆acyloxyC₁-C₆alkoxy,C₂-C₆haloacyloxyC₁-C₆alkoxy, or C₂-C₆acyloxyC₁-C₆haloalkoxy, can beobtained by transformation of a compound of formula (IV-B), wherein R¹,R³ and R⁴ are as defined for formula (I), R¹¹ is hydroxy or halogen andR¹⁴ is C₂-C₆acyloxy, C₂-C₆haloacyloxy, C₁-C₆alkoxyC₁-C₆alkoxy,C₁-C₆haloalkoxyC₁-C₆alkoxy, C₁-C₆alkoxyC₁-C₆haloalkoxy,C₂-C₆acyloxyC₁-C₆alkoxy, C₂-C₆haloacyloxyC₁-C₆alkoxy, orC₂-C₆acyloxyC₁-C₆haloalkoxy, with a compound of formula (V), wherein R⁵,R⁶, R⁷ and R⁸ are as defined for formula (I), and with an acid or abase. This is shown in Scheme 10 below.

The compounds of formula (IV-B), wherein R¹, R³ and R⁴ are as definedfor formula (I) R¹¹ is hydroxy or halogen and R¹⁴ is C₂-C₆acyloxy,C₂-C₆haloacyloxy, C₁-C₆alkoxyC₁-C₆alkoxy, C₁-C₆haloalkoxyC₁-C₆alkoxy,C₁-C₆alkoxyC₁-C₆haloalkoxy, C₂-C₆acyloxyC₁-C₆alkoxy,C₂-C₆haloacyloxyC₁-C₆alkoxy, or C₂-C₆acyloxyC₁-C₆haloalkoxy, can beobtained by transformation of a compound of formula (VIII-B), whereinR¹, R³, and R⁴ are as defined for formula (I), R¹³ is C₁-C₆alkyl and R¹⁴is C₂-C₆acyloxy, C₂-C₆haloacyloxy, C₁-C₆alkoxyC₁-C₆alkoxy,C₁-C₆haloalkoxyC₁-C₆alkoxy, C₁-C₆alkoxyC₁-C₆haloalkoxy,C₂-C₆acyloxyC₁-C₆alkoxy, C₂-C₆haloacyloxyC₁-C₆alkoxy, orC₂-C₆acyloxyC₁-C₆haloalkoxy, and with a base or a halogenation agent.This is shown in Scheme 11 below.

The compounds of formula (VIII-B), wherein R¹, R³, and R⁴ are as definedfor formula (I), R¹³ is C₁-C₆alkyl and R¹⁴ is C₂-C₆acyloxy,C₂-C₆haloacyloxy, C₁-C₆alkoxyC₁-C₆alkoxy, C₁-C₆haloalkoxyC₁-C₆alkoxy,C₁-C₆alkoxyC₁-C₆haloalkoxy, C₂-C₆acyloxyC₁-C₆alkoxy,C₂-C₆haloacyloxyC₁-C₆alkoxy, or C₂-C₆acyloxyC₁-C₆haloalkoxy, can beobtained by transformation of a compound of formula (VIII-A), whereinR¹, R³, and R⁴ are as defined for formula (I) and R¹³ is C₁-C₆alkyl,with a compound of formula (X), wherein R¹⁴ is C₂-C₆acyloxy,C₂-C₆haloacyloxy, C₁-C₆alkoxyC₁-C₆alkoxy, C₁-C₆haloalkoxyC₁-C₆alkoxy,C₁-C₆alkoxyC₁-C₆haloalkoxy, C₂-C₆acyloxyC₁-C₆alkoxy,C₂-C₆haloacyloxyC₁-C₆alkoxy, or C₂-C₆acyloxyC₁-C₆haloalkoxy and R¹⁵ ishalogen, and with a base. This is shown in Scheme 12 below.

Surprisingly, it has now been found that the novel compounds of formula(I) have, for practical purposes, a very advantageous level ofbiological activity for protecting plants against diseases that arecaused by fungi.

The compounds of formula (I) can be used in the agricultural sector andrelated fields of use, e.g., as active ingredients for controlling plantpests or on non-living materials for control of spoilage microorganismsor organisms potentially harmful to man. The novel compounds aredistinguished by excellent activity at low rates of application, bybeing well tolerated by plants and by being environmentally safe. Theyhave very useful curative, preventive and systemic properties and may beused for protecting numerous cultivated plants. The compounds of formula(I) can be used to inhibit or destroy the pests that occur on plants orparts of plants (fruit, blossoms, leaves, stems, tubers, roots) ofdifferent crops of useful plants, while at the same time protecting alsothose parts of the plants that grow later, e.g., from phytopathogenicmicroorganisms.

The present invention further relates to a method for controlling orpreventing infestation of plants or plant propagation material and/orharvested food crops susceptible to microbial attack by treating plantsor plant propagation material and/or harvested food crops wherein aneffective amount a compound of formula (I) is applied to the plants, toparts thereof or the locus thereof.

It is also possible to use the compounds of formula (I) as fungicide.The term “fungicide” as used herein means a compound that controls,modifies, or prevents the growth of fungi. The term “fungicidallyeffective amount” means the quantity of such a compound or combinationof such compounds that is capable of producing an effect on the growthof fungi. Controlling or modifying effects include all deviation fromnatural development, such as killing, retardation and the like, andprevention includes barrier or other defensive formation in or on aplant to prevent fungal infection.

It is also possible to use compounds of formula (I) as dressing agentsfor the treatment of plant propagation material, e.g., seeds, such asfruits, tubers or grains, or plant cuttings (e.g., rice), for theprotection against fungal infections, as well as against phytopathogenicfungi occurring in the soil. The propagation material can be treatedwith a composition comprising a compound of formula (I) before planting:seeds, e.g., can be dressed before being sown.

The active ingredients according to the invention can also be applied tograins (coating), either by impregnating the seeds in a liquidformulation or by coating them with a solid formulation. The compositioncan also be applied to the planting site when the propagation materialis being planted, e.g., to the seed furrow during sowing. The inventionrelates also to such methods of treating plant propagation material andto the plant propagation material so treated.

Furthermore, the compounds according to the present invention can beused for controlling fungi in related areas, for example in theprotection of technical materials, including wood and wood relatedtechnical products, in food storage, in hygiene management.

In addition, the invention could be used to protect non-living materialsfrom fungal attack, e.g., lumber, wall boards and paint.

The compounds of formula (I) may be, for example, effective againstfungi and fungal vectors of disease as well as phytopathogenic bacteriaand viruses. These fungi and fungal vectors of disease as well asphytopathogenic bacteria and viruses are for example: Absidiacorymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp, Aspergillusspp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A.terrus, Aureobasidium spp. including A. pullulans, Blastomycesdermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp.including B. dothidea, B. obtusa, Botrytis spp. including B. cinerea,Candida spp. including C. albicans, C. glabrata, C. krusei, C.lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans,Ceratocystis spp, Cercospora spp. including C. arachidicola,Cercosporidium personatum, Cladosporium spp, Claviceps purpurea,Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C.musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechsleraspp, Elsinoe spp, Epidermophyton spp, Erwinia amylovora, Erysiphe spp.including E. cichoracearum, Eutypa lata, Fusarium spp. including F.culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum,F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis,Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum,Glomerella cingulate, Guignardia bidwellii, Gymnosporangiumjuniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasmaspp. including H. capsulatum, Laetisaria fuciformis, Leptographiumlindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochiumnivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp.including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostomapiceae, Paracoccidioides spp, Penicillium spp. including P. digitatum,P. italicum, Petriellidium spp, Peronosclerospora spp. Including P.maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaerianodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp,Phoma spp, Phomopsis viticola, Phytophthora spp. including P. infestans,Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp.,Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxabetae, Pseudocercosporella herpotrichoides, Pseudomonas spp,Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopezizatracheiphila, Puccinia Spp. including P. hordei, P. recondita, P.striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp,Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum,Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus,Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S.prolificans, Schizothyrium pomi, Sclerotinia spp, Sclerotium spp,Septoria spp, including S. nodorum, S. tritici, Sphaerotheca macularis,Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp,Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephoruscucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp.,including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp,Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturiaspp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.

Within the scope of present invention, target crops and/or useful plantsto be protected typically comprise perennial and annual crops, such asberry plants for example blackberries, blueberries, cranberries,raspberries and strawberries; cereals for example barley, maize (corn),millet, oats, rice, rye, sorghum triticale and wheat; fibre plants forexample cotton, flax, hemp, jute and sisal; field crops for examplesugar and fodder beet, coffee, hops, mustard, oilseed rape (canola),poppy, sugar cane, sunflower, tea and tobacco; fruit trees for exampleapple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pearand plum; grasses for example Bermuda grass, bluegrass, bentgrass,centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass;herbs such as basil, borage, chives, coriander, lavender, lovage, mint,oregano, parsley, rosemary, sage and thyme; legumes for example beans,lentils, peas and soya beans; nuts for example almond, cashew, groundnut, hazelnut, peanut, pecan, pistachio and walnut; palms for exampleoil palm; ornamentals for example flowers, shrubs and trees; othertrees, for example cacao, coconut, olive and rubber; vegetables forexample asparagus, aubergine, broccoli, cabbage, carrot, cucumber,garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin,rhubarb, spinach and tomato; and vines for example grapes.

The term “useful plants” is to be understood as including also usefulplants that have been rendered tolerant to herbicides like bromoxynil orclasses of herbicides (such as, for example, HPPD inhibitors, ALSinhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron,EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS(glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase)inhibitors) as a result of conventional methods of breeding or geneticengineering. An example of a crop that has been rendered tolerant toimidazolinones, e.g. imazamox, by conventional methods of breeding(mutagenesis) is Clearfield® summer rape (Canola). Examples of cropsthat have been rendered tolerant to herbicides or classes of herbicidesby genetic engineering methods include glyphosate- andglufosinate-resistant maize varieties commercially available under thetrade names RoundupReady®, Herculex I® and LibertyLink®.

The term “useful plants” is to be understood as including also usefulplants which have been so transformed by the use of recombinant DNAtechniques that they are capable of synthesising one or more selectivelyacting toxins, such as are known, for example, from toxin-producingbacteria, especially those of the genus Bacillus.

Examples of such plants are: YieldGard® (maize variety that expresses aCryIA(b) toxin); YieldGard Rootworm® (maize variety that expresses aCryIIIB(b1) toxin); YieldGard Plus® (maize variety that expresses aCryIA(b) and a CryIIIB(b1) toxin); Starlink® (maize variety thatexpresses a Cry9(c) toxin); Herculex I® (maize variety that expresses aCryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase(PAT) to achieve tolerance to the herbicide glufosinate ammonium);NuCOTN 33B® (cotton variety that expresses a CryIA(c) toxin); BollgardI® (cotton variety that expresses a CryIA(c) toxin); Bollgard II®(cotton variety that expresses a CryIA(c) and a CryIIA(b) toxin);VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potatovariety that expresses a CryIIIA toxin); NatureGard® Agrisure® GTAdvantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11corn borer (CB) trait), Agrisure® RW (corn rootworm trait) andProtecta®.

The term “crops” is to be understood as including also crop plants whichhave been so transformed by the use of recombinant DNA techniques thatthey are capable of synthesising one or more selectively acting toxins,such as are known, for example, from toxin-producing bacteria,especially those of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, forexample, insecticidal proteins from Bacillus cereus or Bacilluspopilliae; or insecticidal proteins from Bacillus thuringiensis, such as8-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1,Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonisingnematodes, for example Photorhabdus spp. or Xenorhabdus spp., such asPhotorhabdus luminescens, Xenorhabdus nematophilus; toxins produced byanimals, such as scorpion toxins, arachnid toxins, wasp toxins and otherinsect-specific neurotoxins; toxins produced by fungi, such asStreptomycetes toxins, plant lectins, such as pea lectins, barleylectins or snowdrop lectins; agglutinins; proteinase inhibitors, such astrypsin inhibitors, serine protease inhibitors, patatin, cystatin,papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin,maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolismenzymes, such as 3-hydroxysteroidoxidase,ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysoneinhibitors, HMG-COA-reductase, ion channel blockers, such as blockers ofsodium or calcium channels, juvenile hormone esterase, diuretic hormonereceptors, stilbene synthase, bibenzyl synthase, chitinases andglucanases.

In the context of the present invention there are to be understood by8-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for exampleVip1, Vip2, Vip3 or Vip3A, expressly also hybrid toxins, truncatedtoxins and modified toxins. Hybrid toxins are produced recombinantly bya new combination of different domains of those proteins (see, forexample, WO 02/15701). Truncated toxins, for example a truncated Cry1Ab,are known. In the case of modified toxins, one or more amino acids ofthe naturally occurring toxin are replaced. In such amino acidreplacements, preferably non-naturally present protease recognitionsequences are inserted into the toxin, such as, for example, in the caseof Cry3A055, a cathepsin-G-recognition sequence is inserted into a Cry3Atoxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesisingsuch toxins are disclosed, for example, in EP-A-0 374 753, WO 93/07278,WO 95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants aregenerally known to the person skilled in the art and are described, forexample, in the publications mentioned above. CryI-type deoxyribonucleicacids and their preparation are known, for example, from WO 95/34656,EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plantstolerance to harmful insects. Such insects can occur in any taxonomicgroup of insects, but are especially commonly found in the beetles(Coleoptera), two-winged insects (Diptera) and butterflies(Lepidoptera).

Transgenic plants containing one or more genes that code for aninsecticidal resistance and express one or more toxins are known andsome of them are commercially available. Examples of such plants are:YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGardRootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGardPlus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin);Starlink® (maize variety that expresses a Cry9C toxin); Herculex I®(maize variety that expresses a Cry1Fa2 toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to theherbicide glufosinate ammonium); NuCOTN 33B® (cotton variety thatexpresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses aCry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac anda Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and aCry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin);NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait),Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

1. Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a truncated Cry1Ab toxin. Bt11 maize alsotransgenically expresses the enzyme PAT to achieve tolerance to theherbicide glufosinate ammonium.2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Geneticallymodified Zea mays which has been rendered resistant to attack by theEuropean corn borer (Ostrinia nubilalis and Sesamia nonagrioides) bytransgenic expression of a Cry1Ab toxin. Bt176 maize also transgenicallyexpresses the enzyme PAT to achieve tolerance to the herbicideglufosinate ammonium.3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790St. Sauveur, France, registration number C/FR/96/05/10. Maize which hasbeen rendered insect-resistant by transgenic expression of a modifiedCry3A toxin. This toxin is Cry3A055 modified by insertion of acathepsin-G-protease recognition sequence. The preparation of suchtransgenic maize plants is described in WO 03/018810.4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863expresses a Cry3Bb1 toxin and has resistance to certain Coleopterainsects.5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren,B-1150 Brussels, Belgium, registration number C/ES/96/02.6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C/NL/00/10. Geneticallymodified maize for the expression of the protein Cry1F for achievingresistance to certain Lepidoptera insects and of the PAT protein forachieving tolerance to the herbicide glufosinate ammonium.7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue deTervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03.Consists of conventionally bred hybrid maize varieties by crossing thegenetically modified varieties NK603 and MON 810. NK603×MON 810 Maizetransgenically expresses the protein CP4 EPSPS, obtained fromAgrobacterium sp. strain CP4, which imparts tolerance to the herbicideRoundup® (contains glyphosate), and also a Cry1Ab toxin obtained fromBacillus thuringiensis subsp. kurstaki which brings about tolerance tocertain Lepidoptera, include the European corn borer.

The compounds of Formula (I) according to the present invention(including any one of compounds described in Table 2 (below)) may beused in controlling or preventing phytopathogenic diseases, especiallyphytopathogenic fungi (such as Phakopsora pachyrhizi) on soy beanplants.

In particular, transgenic soybean plants expressing toxins, for exampleinsecticidal proteins such as delta-endotoxins, e.g. Cry1Ac (Cry1Ac Btprotein). Accordingly, this may include transgenic soybean plantscomprising event MON87701 (see U.S. Pat. No. 8,049,071 and relatedapplications and patents, as well as WO 2014/170327 A1 (eg, seeparagraph [008] reference to Intacta RR2 PRO™ soybean)), event MON87751(US. Patent Application Publication No. 2014/0373191) or event DAS-81419(U.S. Pat. No. 8,632,978 and related applications and patents).

Other transgenic soybean plants may comprise event SYHTOH2—HPPDtolerance (U.S. Patent Application Publication No. 2014/0201860 andrelated applications and patents), event MON89788-glyphosate tolerance(U.S. Pat. No. 7,632,985 and related applications and patents), eventMON87708—dicamba tolerance (U.S. Patent Application Publication No. US2011/0067134 and related applications and patents), eventDP-356043-5—glyphosate and ALS tolerance (U.S. Patent ApplicationPublication No. US 2010/0184079 and related applications and patents),event A2704-12—glufosinate tolerance (U.S. Patent ApplicationPublication No. US 2008/0320616 and related applications and patents),event DP-305423-1—ALS tolerance (U.S. Patent Application Publication No.US 2008/0312082 and related applications and patents), eventA5547-127—glufosinate tolerance (U.S. Patent Application Publication No.US 2008/0196127 and related applications and patents), eventDAS-40278-9—tolerance to 2,4-dichlorophenoxyacetic acid andaryloxyphenoxypropionate (see WO 2011/022469, WO 2011/022470, WO2011/022471, and related applications and patents), event 127—ALStolerance (WO 2010/080829 and related applications and patents), eventGTS 40-3-2—glyphosate tolerance, eventDAS-68416-4-2,4-dichlorophenoxyacetic acid and glufosinate tolerance,event FG72—glyphosate and isoxaflutole tolerance, event BPS-CV127-9—ALStolerance and GU262—glufosinate tolerance or event SYHT04R—HPPDtolerance.

Under certain circumstances, compounds of Formula (I) according to thepresent invention when used in controlling or preventing phytopathogenicdiseases, especially phytopathogenic fungi (such as Phakopsorapachyrhizi) on soy bean plants (in particular any of the transgenicsoybean plants as described above), may display a synergisticinteraction between the active ingredients.

Additionally, to date, no cross-resistance has been observed between thecompounds of Formula (I) (including any one of compounds described inTable 2 (below)) and the current fungicidal solutions used to controlPhakopsora pachyrhizi.

Indeed, fungicidal-resistant strains of Phakopsora pachyrhizi have beenreported in the scientific literature, with strains resistant to one ormore fungicides from at least each of the following fungicidal mode ofaction classes being observed: sterol demethylation-inhibitors (DMI),quinone-outside-inhibitors (QoI) and succinate dehydrogenase inhibitors(SDHI). See for example: “Sensitivity of Phakopsora pachyrhizi towardsquinone-outside-inhibitors and demethylation-inhibitors, andcorresponding resistance mechanisms.” Schmitz H K et al, Pest Manag Sci(2014) 70: 378-388; “First detection of a SDH variant with reduced SDHIsensitivity in Phakopsora pachyrhizi” Simões K et al, J Plant Dis Prot(2018) 125: 21-2; “Competitive fitness of Phakopsora pachyrhizi isolateswith mutations in the CYP51 and CYTB genes.” Klosowski A C et al,Phytopathology (2016) 106: 1278-1284; “Detection of the F129L mutationin the cytochrome b gene in Phakopsora pachyrhizi.” Klosowski A C et al,Pest Manag Sci (2016) 72: 1211-1215.

Thus, in a preferred embodiment, the compounds of Formula (I) (includingany one of compounds described in Table 2 (below)), or fungicidalcompositions according to the present invention comprising a compound ofFormula (I), are used to control Phakopsora pachyrhizi which areresistant to one or more fungicides from any of the following fungicidalMoA classes: sterol demethylation-inhibitors (DMI),quinone-outside-inhibitors (QoI) and succinate dehydrogenase inhibitors(SDHI).

The compounds of Formula (I) (including any one of compounds describedin Table 2 (below)) or fungicidal compositions according to the presentinvention comprising a compound of Formula (I) may be used incontrolling or preventing phytopathogenic diseases, especiallyphytopathogenic fungi (such as Phakopsora pachyrhizi) on soy beanplants. In particular, there are known in the scientific literaturecertain Elite soybean plant varieties where R-gene stacks, conferring adegree of immunity or resistance to specific Phakopsora pachyrhizi, havebeen been introgressed in the plant genome, see for example: “FightingAsian Soybean Rust”, Langenbach C, et al, Front Plant Science 7(797)2016).

An elite plant is any plant from an elite line, such that an elite plantis a representative plant from an elite variety. Non-limiting examplesof elite soybean varieties that are commercially available to farmers orsoybean breeders include: AG00802, A0868, AG0902, A1923, AG2403, A2824,A3704, A4324, A5404, AG5903, AG6202 AG0934; AG1435; AG2031; AG2035;AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831;AG6534; and AG7231 (Asgrow Seeds, Des Moines, Iowa, USA); BPR0144RR, BPR4077NRR and BPR 4390NRR (Bio Plant Research, Camp Point, Ill., USA);DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, Ill., USA); DP 4546 RR,and DP 7870 RR (Delta & Pine Land Company, Lubbock, Tex., USA); JG03R501, JG 32R606C ADD and JG 55R503C (JGL Inc., Greencastle, Ind.,USA); NKS 13-K2 (NK Division of Syngenta Seeds, Golden Valley, Minn.,USA); 90M01, 91M30, 92M33, 93M11, 94M30, 95M30, 97B52, P008T22R2;P16T17R2; P22T69R; P25T51R; P34T07R2; P35T58R; P39T67R; P47T36R;P46T21R; and P56T03R2 (Pioneer Hi-Bred International, Johnston, Iowa,USA); SG4771NRR and SG5161NRR/STS (Soygenetics, LLC, Lafayette, Ind.,USA); S00-K5, S11-L2, S28-Y2, S43-B1, S53-A1, S76-L9, S78-G6, S0009-M2;S007-Y4; S04-D3; S14-A6; S20-T6; S21-M7; S26-P3; S28-N6; S30-V6; S35-C₃;S36-Y6; S39-C₄; S47-K5; S48-D9; S52-Y2; S58-Z4; S67-R6; S73-S8; andS78-G6 (Syngenta Seeds, Henderson, Ky., USA); Richer (Northstar SeedLtd. Alberta, Calif.); 14RD62 (Stine Seed Co. Ia., USA); or Armor 4744(Armor Seed, LLC, Ar., USA).

Thus, in a further preferred embodiment, the compounds of Formula (I)(including any one of compounds described in Table 2 (below)), orfungicidal compositions according to the present invention comprising acompound of Formula (I), are used to control Phakopsora pachyrhizi,(including fungicidally-resistant strains thereof, as outlined above) onElite soybean plant varieties where R-gene stacks, conferring a degreeof immunity or resistance to specific Phakopsora pachyrhizi, have beenbeen introgressed in the plant genome. Numerous benefits may be expectedto ensue from said use, e.g. improved biological activity, anadvantageous or broader spectrum of activity (inc. sensitive andresistant strains of Phakopsora pachyrhizi), an increased safetyprofile, improved crop tolerance, synergistic interactions orpotentiating properties, improved onset of action or a longer lastingresidual activity, a reduction in the number of applications and/or areduction in the application rate of the compounds and compositionsrequired for effective control of the phytopathogen (Phakopsorapachyrhizi), thereby enabling beneficial resistance-managementpractices, reduced environmental impact and reduced operator exposure.

The term “locus” as used herein means fields in or on which plants aregrowing, or where seeds of cultivated plants are sown, or where seedwill be placed into the soil. It includes soil, seeds, and seedlings, aswell as established vegetation.

The term “plants” refers to all physical parts of a plant, includingseeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, andfruits.

The term “plant propagation material” is understood to denote generativeparts of the plant, such as seeds, which can be used for themultiplication of the latter, and vegetative material, such as cuttingsor tubers, for example potatoes. There may be mentioned for exampleseeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes andparts of plants. Germinated plants and young plants which are to betransplanted after germination or after emergence from the soil, mayalso be mentioned. These young plants may be protected beforetransplantation by a total or partial treatment by immersion. Preferably“plant propagation material” is understood to denote seeds.

Pesticidal agents referred to herein using their common name are known,for example, from “The Pesticide Manual”, 15th Ed., British CropProtection Council 2009.

The compounds of formula (I) may be used in unmodified form or,preferably, together with the adjuvants conventionally employed in theart of formulation. To this end, they may be conveniently formulated inknown manner to emulsifiable concentrates, coatable pastes, directlysprayable or dilutable solutions or suspensions, dilute emulsions,wettable powders, soluble powders, dusts, granulates, and alsoencapsulations e.g. in polymeric substances. As with the type of thecompositions, the methods of application, such as spraying, atomising,dusting, scattering, coating or pouring, are chosen in accordance withthe intended objectives and the prevailing circumstances. Thecompositions may also contain further adjuvants such as stabilizers,antifoams, viscosity regulators, binders or tackifiers as well asfertilizers, micronutrient donors or other formulations for obtainingspecial effects.

Suitable carriers and adjuvants, e.g., for agricultural use, can besolid or liquid and are substances useful in formulation technology,e.g. natural or regenerated mineral substances, solvents, dispersants,wetting agents, tackifiers, thickeners, binders or fertilizers. Suchcarriers are for example described in WO 97/33890.

The compounds of formula (I) are normally used in the form ofcompositions and can be applied to the crop area or plant to be treated,simultaneously or in succession with further compounds. These furthercompounds can be, e.g., fertilizers or micronutrient donors or otherpreparations, which influence the growth of plants. They can also beselective herbicides or non-selective herbicides as well asinsecticides, fungicides, bactericides, nematicides, molluscicides ormixtures of several of these preparations, if desired together withfurther carriers, surfactants or application promoting adjuvantscustomarily employed in the art of formulation.

The compounds of formula (I) may be used in the form of (fungicidal)compositions for controlling or protecting against phytopathogenicmicroorganisms, comprising as active ingredient at least one compound offormula (I) or of at least one preferred individual compound asabove-defined, in free form or in agrochemically usable salt form, andat least one of the above-mentioned adjuvants.

The invention provides a composition, preferably a fungicidalcomposition, comprising at least one compound formula (I) anagriculturally acceptable carrier and optionally an adjuvant. Anagricultural acceptable carrier is for example a carrier that issuitable for agricultural use. Agricultural carriers are well known inthe art. Preferably, said composition may comprise at least one or morepesticidally active compounds, for example an additional fungicidalactive ingredient in addition to the compound of formula (I).

The compound of formula (I) may be the sole active ingredient of acomposition or it may be admixed with one or more additional activeingredients such as a pesticide, fungicide, synergist, herbicide orplant growth regulator where appropriate. An additional activeingredient may, in some cases, result in unexpected synergisticactivities.

Examples of suitable additional active ingredients include the followingacycloamino acid fungicides, aliphatic nitrogen fungicides, amidefungicides, anilide fungicides, antibiotic fungicides, aromaticfungicides, arsenical fungicides, aryl phenyl ketone fungicides,benzamide fungicides, benzanilide fungicides, benzimidazole fungicides,benzothiazole fungicides, botanical fungicides, bridged diphenylfungicides, carbamate fungicides, carbanilate fungicides, conazolefungicides, copper fungicides, dicarboximide fungicides, dinitrophenolfungicides, dithiocarbamate fungicides, dithiolane fungicides, furamidefungicides, furanilide fungicides, hydrazide fungicides, imidazolefungicides, mercury fungicides, morpholine fungicides, organophosphorousfungicides, organotin fungicides, oxathiin fungicides, oxazolefungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazolefungicides, pyridine fungicides, pyrimidine fungicides, pyrrolefungicides, quaternary ammonium fungicides, quinoline fungicides,quinone fungicides, quinoxaline fungicides, strobilurin fungicides,sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides,thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides,triazine fungicides, triazole fungicides, triazolopyrimidine fungicides,urea fungicides, valinamide fungicides, and zinc fungicides.

Examples of suitable additional active ingredients also include thefollowing: 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acidmethoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]-amide,1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (1072957-71-1),1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(4′-methylsulfanyl-biphenyl-2-yl)-amide,1-methyl-3-difluoromethyl-4H-pyrazole-4-carboxylic acid[2-(2,4-dichloro-phenyl)-2-methoxy-1-methyl-ethyl]-amide,(5-Chloro-2,4-dimethyl-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,(5-Bromo-4-chloro-2-methoxy-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,2-{2-[(E)-3-(2,6-Dichloro-phenyl)-1-methyl-prop-2-en-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide,3-[5-(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,(E)-N-methyl-2-[2-(2, 5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide, 4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulphonamide,a-[N-(3-chloro-2, 6-xylyl)-2-methoxyacetamido]-yl-butyrolactone,4-chloro-2-cyano-N, -dimethyl-5-p-tolylimidazole-1-sulfonamide,N-allyl-4,5-dimethyl-2-trimethylsilylthiophene-3-carboxamide,N—(I-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy) propionamide,N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide,(.+−.)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol,2′,6′-dibromo-2-methyl-4-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,1-imidazolyl-1-(4′-chlorophenoxy)-3,3-dimethylbutan-2-one, methyl(E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]3-methoxyacrylate,methyl(E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(5-methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(phenyl-sulphonyloxy)phenoxy]phenyl-3-methoxyacrylate,methyl (E)-2-[2-[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-phenoxyphenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dimethyl-benzoyl)pyrrol-1-yl]-3-methoxyacrylate, methyl(E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(2-phenylethen-1-yl)-phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-3-methoxyacrylate, methyl(E)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methoxyacrylate,methyl(E)-2-(2-[3-(alpha-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylate,methyl (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methoxyacrylate,methyl (E)-2-[2-(3-n-propyloxy-phenoxy)phenyl]3-methoxyacrylate, methyl(E)-2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(2-fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(4-tert-butyl-pyridin-2-yloxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-m ethoxyacrylate, methyl(E)-2-[2-[(3-methyl-pyridin-2-yloxymethyl)phenyl]-3-m ethoxyacrylate,methyl (E)-2-[2-[6-(2-methyl-phenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl (E),(E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloximinomethyl)phenyl]-3-m ethoxyacrylate, methyl(E)-2-{2-[6-(6-methylpyrid in-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-crylate, methyl(E),(E)-2-{2-(3-methoxyphenyl)methyloximinomethyl]-phenyl}-3-methoxyacrylate,methyl(E)-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[6-phenylpyrimidin-4-yl)-methyloximinomethyl]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(4-chlorophenyl)-methyloximinomethyl]-phenyl}-3-methoxyacrylate,methyl(E)-2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(3-nitrophenyl)methyloximinomethyl]phenyl}-3-methoxyacrylate,3-chloro-7-(2-aza-2,7,7-trimethyl-oct-3-en-5-ine),2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 3-iodo-2-propinylalcohol, 4-chlorophenyl-3-iodopropargyl formal,3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 2,3,3-triiodoallylalcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propinyln-butylcarbamate, 3-iodo-2-propinyl n-hexylcarbamate, 3-iodo-2-propinylcyclohexyl-carbamate, 3-iodo-2-propinyl phenylcarbamate; phenolderivatives, such as tribromophenol, tetrachlorophenol,3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol,dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol,2-benzyl-4-chlorophenol, 5-hydroxy-2(5H)-furanone;4,5-dichlorodithiazolinone, 4,5-benzodithiazolinone,4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-1,2-dithiol-3-one,3,5-dimethyl-tetrahydro-1,3,5-thiadiazine-2-thione,N-(2-p-chlorobenzoylethyl)-hexaminium chloride, acibenzolar, acypetacs,alanycarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradin,amisulbrom, amobam, ampropylfos, anilazine, asomate, aureofungin,azaconazole, azafendin, azithiram, azoxystrobin, barium polysulfide,benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron,benthiavalicarb, benthiazole, benzalkonium chloride, benzamacril,benzamorf, benzohydroxamic acid, benzovindiflupyr, berberine,bethoxazin, biloxazol, binapacryl, biphenyl, bitertanol, bithionol,bixafen, blasticidin-S, boscalid, bromothalonil, bromuconazole,bupirimate, buthiobate, butylamine calcium polysulfide, captafol,captan, carbamorph, carbendazim, carbendazim chlorhydrate, carboxin,carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chitosan,chlobenthiazone, chloraniformethan, chloranil, chlorfenazole, chloroneb,chloropicrin, chlorothalonil, chlorozolinate, chlozolinate, climbazole,clotrimazole, clozylacon, copper containing compounds such as copperacetate, copper carbonate, copper hydroxide, copper naphthenate, copperoleate, copper oxychloride, copper oxyquinolate, copper silicate, coppersulphate, copper tallate, copper zinc chromate and Bordeaux mixture,cresol, cufraneb, cuprobam, cuprous oxide, cyazofamid, cyclafuramid,cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole,cyprodinil, dazomet, debacarb, decafentin, dehydroacetic acid,di-2-pyridyl disulphide 1, 1′-dioxide, dichlofluanid, diclomezine,dichlone, dicloran, dichlorophen, dichlozoline, diclobutrazol,diclocymet, diethofencarb, difenoconazole, difenzoquat, diflumetorim,O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimetachlone,dimetconazole, dimethomorph, dimethirimol, diniconazole, diniconazole-M,dinobuton, dinocap, dinocton, dinopenton, dinosulfon, dinoterbon,diphenylamine, dipyrithione, disulfiram, ditalimfos, dithianon,dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodicin,dodine, doguadine, drazoxolon, edifenphos, enestroburin, epoxiconazole,etaconazole, etem, ethaboxam, ethirimol, ethoxyquin, ethilicin, ethyl(Z)—N-benzyl-N([methyl (methyl-thioethylideneamino-oxycarbonyl)amino]thio)-ß-alaninate, etridiazole, famoxadone, fenamidone,fenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid,fenitropan, fenoxanil, fenpiclonil, fenpicoxamid, fenpropidin,fenpropimorph, fenpyrazamine, fentin acetate, fentin hydroxide, ferbam,ferimzone, fluazinam, fludioxonil, flumetover, flumorph, flupicolide,fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole,flusilazole, flusulfamide, flutanil, flutolanil, flutriafol,fluxapyroxad, folpet, formaldehyde, fosetyl, fuberidazole, furalaxyl,furametpyr, furcarbanil, furconazole, furfural, furmecyclox,furophanate, glyodin, griseofulvin, guazatine, halacrinate,hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole,hexylthiofos, hydrargaphen, hydroxyisoxazole, hymexazole, imazalil,imazalil sulphate, imibenconazole, iminoctadine, iminoctadinetriacetate, inezin, iodocarb, ipconazole, ipfentrifluconazole,iprobenfos, iprodione, iprovalicarb, isopropanyl butyl carbamate,isoprothiolane, isopyrazam, isotianil, isovaledione, izopamfos,kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb,mandipropamid, maneb, mebenil, mecarbinzid, mefenoxam,mefentrifluconazole, mepanipyrim, mepronil, mercuric chloride, mercurouschloride, meptyldinocap, metalaxyl, metalaxyl-M, metam, metazoxolon,metconazole, methasulfocarb, methfuroxam, methyl bromide, methyl iodide,methyl isothiocyanate, metiram, metiram-zinc, metominostrobin,metrafenone, metsulfovax, milneb, moroxydine, myclobutanil, myclozolin,nabam, natamycin, neoasozin, nickel dimethyldithiocarbamate,nitrostyrene, nitrothal-iso-propyl, nuarimol, octhilinone, ofurace,organomercury compounds, orysastrobin, osthol, oxadixyl, oxasulfuron,oxathiapiprolin, oxine-copper, oxolinic acid, oxpoconazole, oxycarboxin,parinol, pefurazoate, penconazole, pencycuron, penflufen,pentachlorophenol, penthiopyrad, phenamacril, phenazin oxide,phosdiphen, phosetyl-Al, phosphorus acids, phthalide, picoxystrobin,piperalin, polycarbamate, polyoxin D, polyoxrim, polyram, probenazole,prochloraz, procymidone, propamidine, propamocarb, propiconazole,propineb, propionic acid, proquinazid, prothiocarb, prothioconazole,pydiflumetofen, pyracarbolid, pyraclostrobin, pyrametrostrobin,pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril, pyrifenox,pyrimethanil, pyriofenone, pyroquilon, pyroxychlor, pyroxyfur,pyrrolnitrin, quaternary ammonium compounds, quinacetol, quinazamid,quinconazole, quinomethionate, quinoxyfen, quintozene, rabenzazole,santonin, sedaxane, silthiofam, simeconazole, sipconazole, sodiumpentachlorophenate, spiroxamine, streptomycin, sulphur, sultropen,tebuconazole, tebfloquin, tecloftalam, tecnazene, tecoram,tetraconazole, thiabendazole, thiadifluor, thicyofen, thifluzamide,2-(thiocyanomethylthio) benzothiazole, thiophanate-methyl, thioquinox,thiram, tiadinil, timibenconazole, tioxymid, tolclofos-methyl,tolylfluanid, triadimefon, triadimenol, triamiphos, triarimol,triazbutil, triazoxide, tricyclazole, tridemorph, trifloxystrobin,triflumazole, triforine, triflumizole, triticonazole, uniconazole,urbacide, validamycin, valifenalate, vapam, vinclozolin, zarilamid,zineb, ziram, and zoxamide.

The compounds of the invention may also be used in combination withanthelmintic agents. Such anthelmintic agents include, compoundsselected from the macrocyclic lactone class of compounds such asivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin,selamectin, moxidectin, nemadectin and milbemycin derivatives asdescribed in EP-357460, EP-444964 and EP-594291. Additional anthelminticagents include semisynthetic and biosynthetic avermectin/milbemycinderivatives such as those described in U.S. Pat. No. 5,015,630,WO-9415944 and WO-9522552. Additional anthelmintic agents include thebenzimidazoles such as albendazole, cambendazole, fenbendazole,flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, andother members of the class. Additional anthelmintic agents includeimidazothiazoles and tetrahydropyrimidines such as tetramisole,levamisole, pyrantel pamoate, oxantel or morantel. Additionalanthelmintic agents include flukicides, such as triclabendazole andclorsulon and the cestocides, such as praziquantel and epsiprantel.

The compounds of the invention may be used in combination withderivatives and analogues of the paraherquamide/marcfortine class ofanthelmintic agents, as well as the antiparasitic oxazolines such asthose disclosed in U.S. Pat. Nos. 5,478,855, 4,639,771 and DE-19520936.

The compounds of the invention may be used in combination withderivatives and analogues of the general class of dioxomorpholineantiparasitic agents as described in WO-9615121 and also withanthelmintic active cyclic depsipeptides such as those described inWO-9611945, WO-9319053, WO-9325543, EP-626375, EP-382173, WO-9419334,EP-382173, and EP-503538.

The compounds of the invention may be used in combination with otherectoparasiticides; for example, fipronil; pyrethroids; organophosphates;insect growth regulators such as lufenuron; ecdysone agonists such astebufenozide and the like; neonicotinoids such as imidacloprid and thelike.

The compounds of the invention may be used in combination with terpenealkaloids, for example those described in WO 95/19363 or WO 04/72086,particularly the compounds disclosed therein.

Other examples of such biologically active compounds that the compoundsof the invention may be used in combination with include but are notrestricted to the following: Organophosphates: acephate, azamethiphos,azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos,chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton,demeton-S-methyl, demeton-S-methyl sulphone, dialifos, diazinon,dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos,etrimfos, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion,flupyrazofos, fonofos, formothion, fosthiazate, heptenophos, isazophos,isothioate, isoxathion, malathion, methacriphos, methamidophos,methidathion, methyl-parathion, mevinphos, monocrotophos, naled,omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl,phenthoate, phosalone, phosfolan, phosphocarb, phosmet, phosphamidon,phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos,proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos,sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos,thimeton, triazophos, trichlorfon, vamidothion.

Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate,benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb,ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801,isoprocarb, indoxacarb, methiocarb, methomyl,5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate,bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin,beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer),bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin,cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate,ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate,flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin,lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins(natural products), resmethrin, tetramethrin, transfluthrin,theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin,tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors:benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron,triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole,chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide,tebufenozide; c) juvenoids: pyriproxyfen, methoprene (includingS-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors:spirodiclofen.

Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118,azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl,bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate,chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine,diacloden, diafenthiuron, DBI-3204, dinactin,dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan,ethiprole, ethofenprox, fenazaquin, flumite, MTI-800, fenpyroximate,fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox,fluproxyfen, halofenprox, hydramethylnon, IKI-220, kanemite, NC-196,neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl,propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen,NC-1111, R-195,RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601,silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon,tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad,triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.

Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki,Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenicbacteria, virus and fungi.

Bactericides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penethamate, moloxicam,cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin,benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin,tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel,triclabendazole.

The following mixtures of the compounds of Formula (I) with activeingredients are preferred. The abbreviation “TX” means one compoundselected from the group consisting of the compounds described in Table 1(compounds of Formulae (1.a) to (1.ah)) and the compounds described inTable 2 (below):

-   -   an adjuvant selected from the group of substances consisting of        petroleum oils (alternative name) (628)+TX,    -   an acaricide selected from the group of substances consisting of        1,1-bis(4-chlorophenyl)-2-ethoxyethanol (IUPAC name) (910)+TX,        2,4-dichlorophenyl benzenesulfonate (IUPAC/Chemical Abstracts        name) (1059)+TX, 2-fluoro-N-methyl-N-1-naphthylacetamide (IUPAC        name) (1295)+TX, 4-chlorophenyl phenyl sulfone (IUPAC name)        (981)+TX, abamectin (1)+TX, acequinocyl (3)+TX, acetoprole        [CCN]+TX, acrinathrin (9)+TX, aldicarb (16)+TX, aldoxycarb        (863)+TX, alpha-cypermethrin (202)+TX, amidithion (870)+TX,        amidoflumet [CCN]+TX, amidothioate (872)+TX, amiton (875)+TX,        amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, aramite        (881)+TX, arsenous oxide (882)+TX, AVI 382 (compound code)+TX,        AZ 60541 (compound code)+TX, azinphos-ethyl (44)+TX,        azinphos-methyl (45)+TX, azobenzene (IUPAC name) (888)+TX,        azocyclotin (46)+TX, azothoate (889)+TX, benomyl (62)+TX,        benoxafos (alternative name) [CCN]+TX, benzoximate (71)+TX,        benzyl benzoate (IUPAC name) [CCN]+TX, bifenazate (74)+TX,        bifenthrin (76)+TX, binapacryl (907)+TX, brofenvalerate        (alternative name)+TX, bromocyclen (918)+TX, bromophos (920)+TX,        bromophos-ethyl (921)+TX, bromopropylate (94)+TX, buprofezin        (99)+TX, butocarboxim (103)+TX, butoxycarboxim (104)+TX,        butylpyridaben (alternative name)+TX, calcium polysulfide (IUPAC        name) (111)+TX, camphechlor (941)+TX, carbanolate (943)+TX,        carbaryl (115)+TX, carbofuran (118)+TX, carbophenothion        (947)+TX, CGA 50′439 (development code) (125)+TX, chinomethionat        (126)+TX, chlorbenside (959)+TX, chlordimeform (964)+TX,        chlordimeform hydrochloride (964)+TX, chlorfenapyr (130)+TX,        chlorfenethol (968)+TX, chlorfenson (970)+TX, chlorfensulfide        (971)+TX, chlorfenvinphos (131)+TX, chlorobenzilate (975)+TX,        chloromebuform (977)+TX, chloromethiuron (978)+TX,        chloropropylate (983)+TX, chlorpyrifos (145)+TX,        chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX, cinerin I        (696)+TX, cinerin II (696)+TX, cinerins (696)+TX, clofentezine        (158)+TX, closantel (alternative name) [CCN]+TX, coumaphos        (174)+TX, crotamiton (alternative name) [CCN]+TX, crotoxyphos        (1010)+TX, cufraneb (1013)+TX, cyanthoate (1020)+TX,        cyflumetofen (CAS Reg. No.: 400882-07-7)+TX, cyhalothrin        (196)+TX, cyhexatin (199)+TX, cypermethrin (201)+TX, DCPM        (1032)+TX, DDT (219)+TX, demephion (1037)+TX, demephion-O        (1037)+TX, demephion-S(1037)+TX, demeton (1038)+TX,        demeton-methyl (224)+TX, demeton-O (1038)+TX, demeton-O-methyl        (224)+TX, demeton-S(1038)+TX, demeton-S-methyl (224)+TX,        demeton-S-methylsulfon (1039)+TX, diafenthiuron (226)+TX,        dialifos (1042)+TX, diazinon (227)+TX, dichlofluanid (230)+TX,        dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicofol        (242)+TX, dicrotophos (243)+TX, dienochlor (1071)+TX, dimefox        (1081)+TX, dimethoate (262)+TX, dinactin (alternative name)        (653)+TX, dinex (1089)+TX, dinex-diclexine (1089)+TX, dinobuton        (269)+TX, dinocap (270)+TX, dinocap-4 [CCN]+TX, dinocap-6        [CCN]+TX, dinocton (1090)+TX, dino-penton (1092)+TX, dinosulfon        (1097)+TX, dinoterbon (1098)+TX, dioxathion (1102)+TX, diphenyl        sulfone (IUPAC name) (1103)+TX, disulfiram (alternative name)        [CCN]+TX, disulfoton (278)+TX, DNOC (282)+TX, dofenapyn        (1113)+TX, doramectin (alternative name) [CCN]+TX, endosulfan        (294)+TX, endothion (1121)+TX, EPN (297)+TX, eprinomectin        (alternative name) [CCN]+TX, ethion (309)+TX, ethoate-methyl        (1134)+TX, etoxazole (320)+TX, etrimfos (1142)+TX, fenazaflor        (1147)+TX, fenazaquin (328)+TX, fenbutatin oxide (330)+TX,        fenothiocarb (337)+TX, fenpropathrin (342)+TX, fenpyrad        (alternative name)+TX, fenpyroximate (345)+TX, fenson (1157)+TX,        fentrifanil (1161)+TX, fenvalerate (349)+TX, fipronil (354)+TX,        fluacrypyrim (360)+TX, fluazuron (1166)+TX, flubenzimine        (1167)+TX, flucycloxuron (366)+TX, flucythrinate (367)+TX,        fluenetil (1169)+TX, flufenoxuron (370)+TX, flumethrin (372)+TX,        fluorbenside (1174)+TX, fluvalinate (1184)+TX, FMC 1137        (development code) (1185)+TX, formetanate (405)+TX, formetanate        hydrochloride (405)+TX, formothion (1192)+TX, formparanate        (1193)+TX, gamma-HCH (430)+TX, glyodin (1205)+TX, halfenprox        (424)+TX, heptenophos (432)+TX, hexadecyl        cyclopropanecarboxylate (IUPAC/Chemical Abstracts name)        (1216)+TX, hexythiazox (441)+TX, iodomethane (IUPAC name)        (542)+TX, isocarbophos (alternative name) (473)+TX, isopropyl        O-(methoxyaminothiophosphoryl)salicylate (IUPAC name) (473)+TX,        ivermectin (alternative name) [CCN]+TX, jasmolin 1 (696)+TX,        jasmolin II (696)+TX, jodfenphos (1248)+TX, lindane (430)+TX,        lufenuron (490)+TX, malathion (492)+TX, malonoben (1254)+TX,        mecarbam (502)+TX, mephosfolan (1261)+TX, mesulfen (alternative        name) [CCN]+TX, methacrifos (1266)+TX, methamidophos (527)+TX,        methidathion (529)+TX, methiocarb (530)+TX, methomyl (531)+TX,        methyl bromide (537)+TX, metolcarb (550)+TX, mevinphos (556)+TX,        mexacarbate (1290)+TX, milbemectin (557)+TX, milbemycin oxime        (alternative name) [CCN]+TX, mipafox (1293)+TX, monocrotophos        (561)+TX, morphothion (1300)+TX, moxidectin (alternative name)        [CCN]+TX, naled (567)+TX, NC-184 (compound code)+TX, NC-512        (compound code)+TX, nifluridide (1309)+TX, nikkomycins        (alternative name) [CCN]+TX, nitrilacarb (1313)+TX, nitrilacarb        1:1 zinc chloride complex (1313)+TX, NNI-0101 (compound        code)+TX, NNI-0250 (compound code)+TX, omethoate (594)+TX,        oxamyl (602)+TX, oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX,        pp′-DDT (219)+TX, parathion (615)+TX, permethrin (626)+TX,        petroleum oils (alternative name) (628)+TX, phenkapton        (1330)+TX, phenthoate (631)+TX, phorate (636)+TX, phosalone        (637)+TX, phosfolan (1338)+TX, phosmet (638)+TX, phosphamidon        (639)+TX, phoxim (642)+TX, pirimiphos-methyl (652)+TX,        polychloroterpenes (traditional name) (1347)+TX, polynactins        (alternative name) (653)+TX, proclonol (1350)+TX, profenofos        (662)+TX, promacyl (1354)+TX, propargite (671)+TX, propetamphos        (673)+TX, propoxur (678)+TX, prothidathion (1360)+TX, prothoate        (1362)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX,        pyrethrins (696)+TX, pyridaben (699)+TX, pyridaphenthion        (701)+TX, pyrimidifen (706)+TX, pyrimitate (1370)+TX, quinalphos        (711)+TX, quintiofos (1381)+TX, R-1492 (development code)        (1382)+TX, RA-17 (development code) (1383)+TX, rotenone        (722)+TX, schradan (1389)+TX, sebufos (alternative name)+TX,        selamectin (alternative name) [CCN]+TX, SI-0009 (compound        code)+TX, sophamide (1402)+TX, spirodiclofen (738)+TX,        spiromesifen (739)+TX, SSI-121 (development code) (1404)+TX,        sulfiram (alternative name) [CCN]+TX, sulfluramid (750)+TX,        sulfotep (753)+TX, sulfur (754)+TX, SZI-121 (development code)        (757)+TX, tau-fluvalinate (398)+TX, tebufenpyrad (763)+TX, TEPP        (1417)+TX, terbam (alternative name)+TX, tetrachlorvinphos        (777)+TX, tetradifon (786)+TX, tetranactin (alternative name)        (653)+TX, tetrasul (1425)+TX, thiafenox (alternative name)+TX,        thiocarboxime (1431)+TX, thiofanox (800)+TX, thiometon (801)+TX,        thioquinox (1436)+TX, thuringiensin (alternative name) [CCN]+TX,        triamiphos (1441)+TX, triarathene (1443)+TX, triazophos        (820)+TX, triazuron (alternative name)+TX, trichlorfon (824)+TX,        trifenofos (1455)+TX, trinactin (alternative name) (653)+TX,        vamidothion (847)+TX, vaniliprole [CCN] and YI-5302 (compound        code)+TX,    -   an algicide selected from the group of substances consisting of        bethoxazin [CCN]+TX, copper dioctanoate (IUPAC name) (170)+TX,        copper sulfate (172)+TX, cybutryne [CCN]+TX, dichlone (1052)+TX,        dichlorophen (232)+TX, endothal (295)+TX, fentin (347)+TX,        hydrated lime [CCN]+TX, nabam (566)+TX, quinoclamine (714)+TX,        quinonamid (1379)+TX, simazine (730)+TX, triphenyltin acetate        (IUPAC name) (347) and triphenyltin hydroxide (IUPAC name)        (347)+TX,    -   an anthelmintic selected from the group of substances consisting        of abamectin (1)+TX, crufomate (1011)+TX, doramectin        (alternative name) [CCN]+TX, emamectin (291)+TX, emamectin        benzoate (291)+TX, eprinomectin (alternative name) [CCN]+TX,        ivermectin (alternative name) [CCN]+TX, milbemycin oxime        (alternative name) [CCN]+TX, moxidectin (alternative name)        [CCN]+TX, piperazine [CCN]+TX, selamectin (alternative name)        [CCN]+TX, spinosad (737) and thiophanate (1435)+TX,    -   an avicide selected from the group of substances consisting of        chloralose (127)+TX, endrin (1122)+TX, fenthion (346)+TX,        pyridin-4-amine (IUPAC name) (23) and strychnine (745)+TX,    -   a bactericide selected from the group of substances consisting        of 1-hydroxy-1H-pyridine-2-thione (IUPAC name) (1222)+TX,        4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name)        (748)+TX, 8-hydroxyquinoline sulfate (446)+TX, bronopol (97)+TX,        copper dioctanoate (IUPAC name) (170)+TX, copper hydroxide        (IUPAC name) (169)+TX, cresol [CCN]+TX, dichlorophen (232)+TX,        dipyrithione (1105)+TX, dodicin (1112)+TX, fenaminosulf        (1144)+TX, formaldehyde (404)+TX, hydrargaphen (alternative        name) [CCN]+TX, kasugamycin (483)+TX, kasugamycin hydrochloride        hydrate (483)+TX, nickel bis(dimethyldithiocarbamate) (IUPAC        name) (1308)+TX, nitrapyrin (580)+TX, octhilinone (590)+TX,        oxolinic acid (606)+TX, oxytetracycline (611)+TX, potassium        hydroxyquinoline sulfate (446)+TX, probenazole (658)+TX,        streptomycin (744)+TX, streptomycin sesquisulfate (744)+TX,        tecloftalam (766)+TX, and thiomersal (alternative name)        [CCN]+TX,    -   a biological agent selected from the group of substances        consisting of Adoxophyes orana GV (alternative name) (12)+TX,        Agrobacterium radiobacter (alternative name) (13)+TX, Amblyseius        spp. (alternative name) (19)+TX, Anagrapha falcifera NPV        (alternative name) (28)+TX, Anagrus atomus (alternative name)        (29)+TX, Aphelinus abdominalis (alternative name) (33)+TX,        Aphidius colemani (alternative name) (34)+TX, Aphidoletes        aphidimyza (alternative name) (35)+TX, Autographa californica        NPV (alternative name) (38)+TX, Bacillus firmus (alternative        name) (48)+TX, Bacillus sphaericus Neide (scientific name)        (49)+TX, Bacillus thuringiensis Berliner (scientific name)        (51)+TX, Bacillus thuringiensis subsp. aizawai (scientific name)        (51)+TX, Bacillus thuringiensis subsp. israelensis (scientific        name) (51)+TX, Bacillus thuringiensis subsp. japonensis        (scientific name) (51)+TX, Bacillus thuringiensis subsp.        kurstaki (scientific name) (51)+TX, Bacillus thuringiensis        subsp. tenebrionis (scientific name) (51)+TX, Beauveria bassiana        (alternative name) (53)+TX, Beauveria brongniartii (alternative        name) (54)+TX, Chrysoperla carnea (alternative name) (151)+TX,        Cryptolaemus montrouzieri (alternative name) (178)+TX, Cydia        pomonella GV (alternative name) (191)+TX, Dacnusa sibirica        (alternative name) (212)+TX, Diglyphus isaea (alternative name)        (254)+TX, Encarsia formosa (scientific name) (293)+TX,        Eretmocerus eremicus (alternative name) (300)+TX, Helicoverpa        zea NPV (alternative name) (431)+TX, Heterorhabditis        bacteriophora and H. megidis (alternative name) (433)+TX,        Hippodamia convergens (alternative name) (442)+TX, Leptomastix        dactylopii (alternative name) (488)+TX, Macrolophus caliginosus        (alternative name) (491)+TX, Mamestra brassicae NPV (alternative        name) (494)+TX, Metaphycus helvolus (alternative name) (522)+TX,        Metarhizium anisopliae var. acridum (scientific name) (523)+TX,        Metarhizium anisopliae var. anisopliae (scientific name)        (523)+TX, Neodiprion sertifer NPV and N. lecontei NPV        (alternative name) (575)+TX, Orius spp. (alternative name)        (596)+TX, Paecilomyces fumosoroseus (alternative name) (613)+TX,        Phytoseiulus persimilis (alternative name) (644)+TX, Spodoptera        exigua multicapsid nuclear polyhedrosis virus (scientific name)        (741)+TX, Steinernema bibionis (alternative name) (742)+TX,        Steinernema carpocapsae (alternative name) (742)+TX, Steinernema        feltiae (alternative name) (742)+TX, Steinernema glaseri        (alternative name) (742)+TX, Steinernema riobrave (alternative        name) (742)+TX, Steinernema riobravis (alternative name)        (742)+TX, Steinernema scapterisci (alternative name) (742)+TX,        Steinernema spp. (alternative name) (742)+TX, Trichogramma spp.        (alternative name) (826)+TX, Typhlodromus occidentalis        (alternative name) (844) and Verticillium lecanii (alternative        name) (848)+TX, Bacillus subtilis var. amyloliquefaciens Strain        FZB24 (available from Novozymes Biologicals Inc., 5400 Corporate        Circle, Salem, Va. 24153, U.S.A. and known under the trade name        Taegro®)+TX,    -   a soil sterilant selected from the group of substances        consisting of iodomethane (IUPAC name) (542) and methyl bromide        (537)+TX,    -   a chemosterilant selected from the group of substances        consisting of apholate [CCN]+TX, bisazir (alternative name)        [CCN]+TX, busulfan (alternative name) [CCN]+TX, diflubenzuron        (250)+TX, dimatif (alternative name) [CCN]+TX, hemel [CCN]+TX,        hempa [CCN]+TX, metepa [CCN]+TX, methiotepa [CCN]+TX, methyl        apholate [CCN]+TX, morzid [CCN]+TX, penfluron (alternative name)        [CCN]+TX, tepa [CCN]+TX, thiohempa (alternative name) [CCN]+TX,        thiotepa (alternative name) [CCN]+TX, tretamine (alternative        name) [CCN] and uredepa (alternative name) [CCN]+TX,    -   an insect pheromone selected from the group of substances        consisting of (E)-dec-5-en-1-yl acetate with (E)-dec-5-en-1-ol        (IUPAC name) (222)+TX, (E)-tridec-4-en-1-yl acetate (IUPAC name)        (829)+TX, (E)-6-methylhept-2-en-4-ol (IUPAC name) (541)+TX,        (E,Z)-tetradeca-4,10-dien-1-yl acetate (IUPAC name) (779)+TX,        (Z)-dodec-7-en-1-yl acetate (IUPAC name) (285)+TX,        (Z)-hexadec-11-enal (IUPAC name) (436)+TX,        (Z)-hexadec-11-en-1-yl acetate (IUPAC name) (437)+TX,        (Z)-hexadec-13-en-11-yn-1-yl acetate (IUPAC name) (438)+TX,        (Z)-icos-13-en-10-one (IUPAC name) (448)+TX,        (Z)-tetradec-7-en-1-al (IUPAC name) (782)+TX,        (Z)-tetradec-9-en-1-ol (IUPAC name) (783)+TX,        (Z)-tetradec-9-en-1-yl acetate (IUPAC name) (784)+TX,        (7E,9Z)-dodeca-7,9-dien-1-yl acetate (IUPAC name) (283)+TX,        (9Z,11E)-tetradeca-9,11-dien-1-yl acetate (IUPAC name) (780)+TX,        (9Z,12E)-tetradeca-9,12-dien-1-yl acetate (IUPAC name) (781)+TX,        14-methyloctadec-1-ene (IUPAC name) (545)+TX, 4-methylnonan-5-ol        with 4-methylnonan-5-one (IUPAC name) (544)+TX,        alpha-multistriatin (alternative name) [CCN]+TX, brevicomin        (alternative name) [CCN]+TX, codlelure (alternative name)        [CCN]+TX, codlemone (alternative name) (167)+TX, cuelure        (alternative name) (179)+TX, disparlure (277)+TX,        dodec-8-en-1-yl acetate (IUPAC name) (286)+TX, dodec-9-en-1-yl        acetate (IUPAC name) (287)+TX, dodeca-8+TX, 10-dien-1-yl acetate        (IUPAC name) (284)+TX, dominicalure (alternative name) [CCN]+TX,        ethyl 4-methyloctanoate (IUPAC name) (317)+TX, eugenol        (alternative name) [CCN]+TX, frontalin (alternative name)        [CCN]+TX, gossyplure (alternative name) (420)+TX, grandlure        (421)+TX, grandlure I (alternative name) (421)+TX, grandlure II        (alternative name) (421)+TX, grandlure III (alternative name)        (421)+TX, grandlure IV (alternative name) (421)+TX, hexalure        [CCN]+TX, ipsdienol (alternative name) [CCN]+TX, ipsenol        (alternative name) [CCN]+TX, japonilure (alternative name)        (481)+TX, lineatin (alternative name) [CCN]+TX, litlure        (alternative name) [CCN]+TX, looplure (alternative name)        [CCN]+TX, medlure [CCN]+TX, megatomoic acid (alternative name)        [CCN]+TX, methyl eugenol (alternative name) (540)+TX, muscalure        (563)+TX, octadeca-2,13-dien-1-yl acetate (IUPAC name) (588)+TX,        octadeca-3,13-dien-1-yl acetate (IUPAC name) (589)+TX, orfralure        (alternative name) [CCN]+TX, oryctalure (alternative name)        (317)+TX, ostramone (alternative name) [CCN]+TX, siglure        [CCN]+TX, sordidin (alternative name) (736)+TX, sulcatol        (alternative name) [CCN]+TX, tetradec-11-en-1-yl acetate (IUPAC        name) (785)+TX, trimedlure (839)+TX, trimedlure A (alternative        name) (839)+TX, trimedlure B₁ (alternative name) (839)+TX,        trimedlure B₂ (alternative name) (839)+TX, trimedlure C        (alternative name) (839) and trunc-call (alternative name)        [CCN]+TX,    -   an insect repellent selected from the group of substances        consisting of 2-(octylthio)ethanol (IUPAC name) (591)+TX,        butopyronoxyl (933)+TX, butoxy(polypropylene glycol) (936)+TX,        dibutyl adipate (IUPAC name) (1046)+TX, dibutyl phthalate        (1047)+TX, dibutyl succinate (IUPAC name) (1048)+TX,        diethyltoluamide [CCN]+TX, dimethyl carbate [CCN]+TX, dimethyl        phthalate [CCN]+TX, ethyl hexanediol (1137)+TX, hexamide        [CCN]+TX, methoquin-butyl (1276)+TX, methylneodecanamide        [CCN]+TX, oxamate [CCN] and picaridin [CCN]+TX,    -   an insecticide selected from the group of substances consisting        of 1-dichloro-1-nitroethane (IUPAC/Chemical Abstracts name)        (1058)+TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane (IUPAC        name) (1056), +TX, 1,2-dichloropropane (IUPAC/Chemical Abstracts        name) (1062)+TX, 1,2-dichloropropane with 1,3-dichloropropene        (IUPAC name) (1063)+TX, 1-bromo-2-chloroethane (IUPAC/Chemical        Abstracts name) (916)+TX,        2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate (IUPAC name)        (1451)+TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl        phosphate (IUPAC name) (1066)+TX, 2-(1,3-dithiolan-2-yl)phenyl        dimethylcarbamate (IUPAC/Chemical Abstracts name) (1109)+TX,        2-(2-butoxyethoxy)ethyl thiocyanate (IUPAC/Chemical Abstracts        name) (935)+TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl        methylcarbamate (IUPAC/Chemical Abstracts name) (1084)+TX,        2-(4-chloro-3,5-xylyloxy)ethanol (IUPAC name) (986)+TX,        2-chlorovinyl diethyl phosphate (IUPAC name) (984)+TX,        2-imidazolidone (IUPAC name) (1225)+TX,        2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX,        2-methyl(prop-2-ynyl)aminophenyl methylcarbamate (IUPAC name)        (1284)+TX, 2-thiocyanatoethyl laurate (IUPAC name) (1433)+TX,        3-bromo-1-chloroprop-1-ene (IUPAC name) (917)+TX,        3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate (IUPAC name)        (1283)+TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate        (IUPAC name) (1285)+TX, 5,5-dimethyl-3-oxocyclohex-1-enyl        dimethylcarbamate (IUPAC name) (1085)+TX, abamectin (1)+TX,        acephate (2)+TX, acetamiprid (4)+TX, acethion (alternative name)        [CCN]+TX, acetoprole [CCN]+TX, acrinathrin (9)+TX, acrylonitrile        (IUPAC name) (861)+TX, alanycarb (15)+TX, aldicarb (16)+TX,        aldoxycarb (863)+TX, aldrin (864)+TX, allethrin (17)+TX,        allosamidin (alternative name) [CCN]+TX, allyxycarb (866)+TX,        alpha-cypermethrin (202)+TX, alpha-ecdysone (alternative name)        [CCN]+TX, aluminium phosphide (640)+TX, amidithion (870)+TX,        amidothioate (872)+TX, aminocarb (873)+TX, amiton (875)+TX,        amiton hydrogen oxalate (875)+TX, amitraz (24)+TX, anabasine        (877)+TX, athidathion (883)+TX, AVI 382 (compound code)+TX, AZ        60541 (compound code)+TX, azadirachtin (alternative name)        (41)+TX, azamethiphos (42)+TX, azinphos-ethyl (44)+TX,        azinphos-methyl (45)+TX, azothoate (889)+TX, Bacillus        thuringiensis delta endotoxins (alternative name) (52)+TX,        barium hexafluorosilicate (alternative name) [CCN]+TX, barium        polysulfide (IUPAC/Chemical Abstracts name) (892)+TX, barthrin        [CCN]+TX, Bayer 22/190 (development code) (893)+TX, Bayer 22408        (development code) (894)+TX, bendiocarb (58)+TX, benfuracarb        (60)+TX, bensultap (66)+TX, beta-cyfluthrin (194)+TX,        beta-cypermethrin (203)+TX, bifenthrin (76)+TX, bioallethrin        (78)+TX, bioallethrin S-cyclopentenyl isomer (alternative name)        (79)+TX, bioethanomethrin [CCN]+TX, biopermethrin (908)+TX,        bioresmethrin (80)+TX, bis(2-chloroethyl) ether (IUPAC name)        (909)+TX, bistrifluron (83)+TX, borax (86)+TX, brofenvalerate        (alternative name)+TX, bromfenvinfos (914)+TX, bromocyclen        (918)+TX, bromo-DDT (alternative name) [CCN]+TX, bromophos        (920)+TX, bromophos-ethyl (921)+TX, bufencarb (924)+TX,        buprofezin (99)+TX, butacarb (926)+TX, butathiofos (927)+TX,        butocarboxim (103)+TX, butonate (932)+TX, butoxycarboxim        (104)+TX, butylpyridaben (alternative name)+TX, cadusafos        (109)+TX, calcium arsenate [CCN]+TX, calcium cyanide (444)+TX,        calcium polysulfide (IUPAC name) (111)+TX, camphechlor (941)+TX,        carbanolate (943)+TX, carbaryl (115)+TX, carbofuran (118)+TX,        carbon disulfide (IUPAC/Chemical Abstracts name) (945)+TX,        carbon tetrachloride (IUPAC name) (946)+TX, carbophenothion        (947)+TX, carbosulfan (119)+TX, cartap (123)+TX, cartap        hydrochloride (123)+TX, cevadine (alternative name) (725)+TX,        chlorbicyclen (960)+TX, chlordane (128)+TX, chlordecone        (963)+TX, chlordimeform (964)+TX, chlordimeform hydrochloride        (964)+TX, chlorethoxyfos (129)+TX, chlorfenapyr (130)+TX,        chlorfenvinphos (131)+TX, chlorfluazuron (132)+TX, chlormephos        (136)+TX, chloroform [CCN]+TX, chloropicrin (141)+TX,        chlorphoxim (989)+TX, chlorprazophos (990)+TX, chlorpyrifos        (145)+TX, chlorpyrifos-methyl (146)+TX, chlorthiophos (994)+TX,        chromafenozide (150)+TX, cinerin 1 (696)+TX, cinerin II        (696)+TX, cinerins (696)+TX, cis-resmethrin (alternative        name)+TX, cismethrin (80)+TX, clocythrin (alternative name)+TX,        cloethocarb (999)+TX, closantel (alternative name) [CCN]+TX,        clothianidin (165)+TX, copper acetoarsenite [CCN]+TX, copper        arsenate [CCN]+TX, copper oleate [CCN]+TX, coumaphos (174)+TX,        coumithoate (1006)+TX, crotamiton (alternative name) [CCN]+TX,        crotoxyphos (1010)+TX, crufomate (1011)+TX, cryolite        (alternative name) (177)+TX, CS 708 (development code)        (1012)+TX, cyanofenphos (1019)+TX, cyanophos (184)+TX,        cyanthoate (1020)+TX, cyclethrin [CCN]+TX, cycloprothrin        (188)+TX, cyfluthrin (193)+TX, cyhalothrin (196)+TX,        cypermethrin (201)+TX, cyphenothrin (206)+TX, cyromazine        (209)+TX, cythioate (alternative name) [CCN]+TX, d-limonene        (alternative name) [CCN]+TX, d-tetramethrin (alternative name)        (788)+TX, DAEP (1031)+TX, dazomet (216)+TX, DDT (219)+TX,        decarbofuran (1034)+TX, deltamethrin (223)+TX, demephion        (1037)+TX, demephion-O (1037)+TX, demephion-S(1037)+TX, demeton        (1038)+TX, demeton-methyl (224)+TX, demeton-O (1038)+TX,        demeton-O-methyl (224)+TX, demeton-S (1038)+TX, demeton-S-methyl        (224)+TX, demeton-S-methylsulphon (1039)+TX, diafenthiuron        (226)+TX, dialifos (1042)+TX, diamidafos (1044)+TX, diazinon        (227)+TX, dicapthon (1050)+TX, dichlofenthion (1051)+TX,        dichlorvos (236)+TX, dicliphos (alternative name)+TX, dicresyl        (alternative name) [CCN]+TX, dicrotophos (243)+TX, dicyclanil        (244)+TX, dieldrin (1070)+TX, diethyl 5-methylpyrazol-3-yl        phosphate (IUPAC name) (1076)+TX, diflubenzuron (250)+TX, dilor        (alternative name) [CCN]+TX, dimefluthrin [CCN]+TX, dimefox        (1081)+TX, dimetan (1085)+TX, dimethoate (262)+TX, dimethrin        (1083)+TX, dimethylvinphos (265)+TX, dimetilan (1086)+TX, dinex        (1089)+TX, dinex-diclexine (1089)+TX, dinoprop (1093)+TX,        dinosam (1094)+TX, dinoseb (1095)+TX, dinotefuran (271)+TX,        diofenolan (1099)+TX, dioxabenzofos (1100)+TX, dioxacarb        (1101)+TX, dioxathion (1102)+TX, disulfoton (278)+TX,        dithicrofos (1108)+TX, DNOC (282)+TX, doramectin (alternative        name) [CCN]+TX, DSP (1115)+TX, ecdysterone (alternative name)        [CCN]+TX, El 1642 (development code) (1118)+TX, emamectin        (291)+TX, emamectin benzoate (291)+TX, EMPC (1120)+TX,        empenthrin (292)+TX, endosulfan (294)+TX, endothion (1121)+TX,        endrin (1122)+TX, EPBP (1123)+TX, EPN (297)+TX, epofenonane        (1124)+TX, eprinomectin (alternative name) [CCN]+TX,        esfenvalerate (302)+TX, etaphos (alternative name) [CCN]+TX,        ethiofencarb (308)+TX, ethion (309)+TX, ethiprole (310)+TX,        ethoate-methyl (1134)+TX, ethoprophos (312)+TX, ethyl formate        (IUPAC name) [CCN]+TX, ethyl-DDD (alternative name) (1056)+TX,        ethylene dibromide (316)+TX, ethylene dichloride (chemical name)        (1136)+TX, ethylene oxide [CCN]+TX, etofenprox (319)+TX,        etrimfos (1142)+TX, EXD (1143)+TX, famphur (323)+TX, fenamiphos        (326)+TX, fenazaflor (1147)+TX, fenchlorphos (1148)+TX,        fenethacarb (1149)+TX, fenfluthrin (1150)+TX, fenitrothion        (335)+TX, fenobucarb (336)+TX, fenoxacrim (1153)+TX, fenoxycarb        (340)+TX, fenpirithrin (1155)+TX, fenpropathrin (342)+TX,        fenpyrad (alternative name)+TX, fensulfothion (1158)+TX,        fenthion (346)+TX, fenthion-ethyl [CCN]+TX, fenvalerate        (349)+TX, fipronil (354)+TX, flonicamid (358)+TX, flubendiamide        (CAS. Reg. No.: 272451-65-7)+TX, flucofuron (1168)+TX,        flucycloxuron (366)+TX, flucythrinate (367)+TX, fluenetil        (1169)+TX, flufenerim [CCN]+TX, flufenoxuron (370)+TX,        flufenprox (1171)+TX, flumethrin (372)+TX, fluvalinate        (1184)+TX, FMC 1137 (development code) (1185)+TX, fonofos        (1191)+TX, formetanate (405)+TX, formetanate hydrochloride        (405)+TX, formothion (1192)+TX, formparanate (1193)+TX,        fosmethilan (1194)+TX, fospirate (1195)+TX, fosthiazate        (408)+TX, fosthietan (1196)+TX, furathiocarb (412)+TX, furethrin        (1200)+TX, gamma-cyhalothrin (197)+TX, gamma-HCH (430)+TX,        guazatine (422)+TX, guazatine acetates (422)+TX, GY-81        (development code) (423)+TX, halfenprox (424)+TX, halofenozide        (425)+TX, HCH (430)+TX, HEOD (1070)+TX, heptachlor (1211)+TX,        heptenophos (432)+TX, heterophos [CCN]+TX, hexaflumuron        (439)+TX, HHDN (864)+TX, hydramethylnon (443)+TX, hydrogen        cyanide (444)+TX, hydroprene (445)+TX, hyquincarb (1223)+TX,        imidacloprid (458)+TX, imiprothrin (460)+TX, indoxacarb        (465)+TX, iodomethane (IUPAC name) (542)+TX, IPSP (1229)+TX,        isazofos (1231)+TX, isobenzan (1232)+TX, isocarbophos        (alternative name) (473)+TX, isodrin (1235)+TX, isofenphos        (1236)+TX, isolane (1237)+TX, isoprocarb (472)+TX, isopropyl        O-(methoxy-aminothiophosphoryl)salicylate (IUPAC name) (473)+TX,        isoprothiolane (474)+TX, isothioate (1244)+TX, isoxathion        (480)+TX, ivermectin (alternative name) [CCN]+TX, jasmolin I        (696)+TX, jasmolin II (696)+TX, jodfenphos (1248)+TX, juvenile        hormone I (alternative name) [CCN]+TX, juvenile hormone II        (alternative name) [CCN]+TX, juvenile hormone III (alternative        name) [CCN]+TX, kelevan (1249)+TX, kinoprene (484)+TX,        lambda-cyhalothrin (198)+TX, lead arsenate [CCN]+TX, lepimectin        (CCN)+TX, leptophos (1250)+TX, lindane (430)+TX, lirimfos        (1251)+TX, lufenuron (490)+TX, lythidathion (1253)+TX, m-cumenyl        methylcarbamate (IUPAC name) (1014)+TX, magnesium phosphide        (IUPAC name) (640)+TX, malathion (492)+TX, malonoben (1254)+TX,        mazidox (1255)+TX, mecarbam (502)+TX, mecarphon (1258)+TX,        menazon (1260)+TX, mephosfolan (1261)+TX, mercurous chloride        (513)+TX, mesulfenfos (1263)+TX, metaflumizone (CCN)+TX, metam        (519)+TX, metam-potassium (alternative name) (519)+TX,        metam-sodium (519)+TX, methacrifos (1266)+TX, methamidophos        (527)+TX, methanesulfonyl fluoride (IUPAC/Chemical Abstracts        name) (1268)+TX, methidathion (529)+TX, methiocarb (530)+TX,        methocrotophos (1273)+TX, methomyl (531)+TX, methoprene        (532)+TX, methoquin-butyl (1276)+TX, methothrin (alternative        name) (533)+TX, methoxychlor (534)+TX, methoxyfenozide (535)+TX,        methyl bromide (537)+TX, methyl isothiocyanate (543)+TX,        methylchloroform (alternative name) [CCN]+TX, methylene chloride        [CCN]+TX, metofluthrin [CCN]+TX, metolcarb (550)+TX,        metoxadiazone (1288)+TX, mevinphos (556)+TX, mexacarbate        (1290)+TX, milbemectin (557)+TX, milbemycin oxime (alternative        name) [CCN]+TX, mipafox (1293)+TX, mirex (1294)+TX,        monocrotophos (561)+TX, morphothion (1300)+TX, moxidectin        (alternative name) [CCN]+TX, naftalofos (alternative name)        [CCN]+TX, naled (567)+TX, naphthalene (IUPAC/Chemical Abstracts        name) (1303)+TX, NC-170 (development code) (1306)+TX, NC-184        (compound code)+TX, nicotine (578)+TX, nicotine sulfate        (578)+TX, nifluridide (1309)+TX, nitenpyram (579)+TX, nithiazine        (1311)+TX, nitrilacarb (1313)+TX, nitrilacarb 1:1 zinc chloride        complex (1313)+TX, NNI-0101 (compound code)+TX, NNI-0250        (compound code)+TX, nornicotine (traditional name) (1319)+TX,        novaluron (585)+TX, noviflumuron (586)+TX,        O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate (IUPAC        name) (1057)+TX, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl        phosphorothioate (IUPAC name) (1074)+TX, O,O-diethyl        O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate (IUPAC name)        (1075)+TX, O,O,O′,O′-tetrapropyl dithiopyrophosphate (IUPAC        name) (1424)+TX, oleic acid (IUPAC name) (593)+TX, omethoate        (594)+TX, oxamyl (602)+TX, oxydemeton-methyl (609)+TX,        oxydeprofos (1324)+TX, oxydisulfoton (1325)+TX, pp′-DDT        (219)+TX, para-dichlorobenzene [CCN]+TX, parathion (615)+TX,        parathion-methyl (616)+TX, penfluron (alternative name)        [CCN]+TX, pentachlorophenol (623)+TX, pentachlorophenyl laurate        (IUPAC name) (623)+TX, permethrin (626)+TX, petroleum oils        (alternative name) (628)+TX, PH 60-38 (development code)        (1328)+TX, phenkapton (1330)+TX, phenothrin (630)+TX, phenthoate        (631)+TX, phorate (636)+TX, phosalone (637)+TX, phosfolan        (1338)+TX, phosmet (638)+TX, phosnichlor (1339)+TX, phosphamidon        (639)+TX, phosphine (IUPAC name) (640)+TX, phoxim (642)+TX,        phoxim-methyl (1340)+TX, pirimetaphos (1344)+TX, pirimicarb        (651)+TX, pirimiphos-ethyl (1345)+TX, pirimiphos-methyl        (652)+TX, polychlorodicyclopentadiene isomers (IUPAC name)        (1346)+TX, polychloroterpenes (traditional name) (1347)+TX,        potassium arsenite [CCN]+TX, potassium thiocyanate [CCN]+TX,        prallethrin (655)+TX, precocene I (alternative name) [CCN]+TX,        precocene II (alternative name) [CCN]+TX, precocene III        (alternative name) [CCN]+TX, primidophos (1349)+TX, profenofos        (662)+TX, profluthrin [CCN]+TX, promacyl (1354)+TX, promecarb        (1355)+TX, propaphos (1356)+TX, propetamphos (673)+TX, propoxur        (678)+TX, prothidathion (1360)+TX, prothiofos (686)+TX,        prothoate (1362)+TX, protrifenbute [CCN]+TX, pymetrozine        (688)+TX, pyraclofos (689)+TX, pyrazophos (693)+TX, pyresmethrin        (1367)+TX, pyrethrin I (696)+TX, pyrethrin II (696)+TX,        pyrethrins (696)+TX, pyridaben (699)+TX, pyridalyl (700)+TX,        pyridaphenthion (701)+TX, pyrimidifen (706)+TX, pyrimitate        (1370)+TX, pyriproxyfen (708)+TX, quassia (alternative name)        [CCN]+TX, quinalphos (711)+TX, quinalphos-methyl (1376)+TX,        quinothion (1380)+TX, quintiofos (1381)+TX, R-1492 (development        code) (1382)+TX, rafoxanide (alternative name) [CCN]+TX,        resmethrin (719)+TX, rotenone (722)+TX, RU 15525 (development        code) (723)+TX, RU 25475 (development code) (1386)+TX, ryania        (alternative name) (1387)+TX, ryanodine (traditional name)        (1387)+TX, sabadilla (alternative name) (725)+TX, schradan        (1389)+TX, sebufos (alternative name)+TX, selamectin        (alternative name) [CCN]+TX, SI-0009 (compound code)+TX, SI-0205        (compound code)+TX, SI-0404 (compound code)+TX, SI-0405        (compound code)+TX, silafluofen (728)+TX, SN 72129 (development        code) (1397)+TX, sodium arsenite [CCN]+TX, sodium cyanide        (444)+TX, sodium fluoride (IUPAC/Chemical Abstracts name)        (1399)+TX, sodium hexafluorosilicate (1400)+TX, sodium        pentachlorophenoxide (623)+TX, sodium selenate (IUPAC name)        (1401)+TX, sodium thiocyanate [CCN]+TX, sophamide (1402)+TX,        spinosad (737)+TX, spiromesifen (739)+TX, spirotetrmat (CCN)+TX,        sulcofuron (746)+TX, sulcofuron-sodium (746)+TX, sulfluramid        (750)+TX, sulfotep (753)+TX, sulfuryl fluoride (756)+TX,        sulprofos (1408)+TX, tar oils (alternative name) (758)+TX,        tau-fluvalinate (398)+TX, tazimcarb (1412)+TX, TDE (1414)+TX,        tebufenozide (762)+TX, tebufenpyrad (763)+TX, tebupirimfos        (764)+TX, teflubenzuron (768)+TX, tefluthrin (769)+TX, temephos        (770)+TX, TEPP (1417)+TX, terallethrin (1418)+TX, terbam        (alternative name)+TX, terbufos (773)+TX, tetrachloroethane        [CCN]+TX, tetrachlorvinphos (777)+TX, tetramethrin (787)+TX,        theta-cypermethrin (204)+TX, thiacloprid (791)+TX, thiafenox        (alternative name)+TX, thiamethoxam (792)+TX, thicrofos        (1428)+TX, thiocarboxime (1431)+TX, thiocyclam (798)+TX,        thiocyclam hydrogen oxalate (798)+TX, thiodicarb (799)+TX,        thiofanox (800)+TX, thiometon (801)+TX, thionazin (1434)+TX,        thiosultap (803)+TX, thiosultap-sodium (803)+TX, thuringiensin        (alternative name) [CCN]+TX, tolfenpyrad (809)+TX, tralomethrin        (812)+TX, transfluthrin (813)+TX, transpermethrin (1440)+TX,        triamiphos (1441)+TX, triazamate (818)+TX, triazophos (820)+TX,        triazuron (alternative name)+TX, trichlorfon (824)+TX,        trichlormetaphos-3 (alternative name) [CCN]+TX, trichloronat        (1452)+TX, trifenofos (1455)+TX, triflumuron (835)+TX,        trimethacarb (840)+TX, triprene (1459)+TX, vamidothion (847)+TX,        vaniliprole [CCN]+TX, veratridine (alternative name) (725)+TX,        veratrine (alternative name) (725)+TX, XMC (853)+TX, xylylcarb        (854)+TX, YI-5302 (compound code)+TX, zeta-cypermethrin        (205)+TX, zetamethrin (alternative name)+TX, zinc phosphide        (640)+TX, zolaprofos (1469) and ZXI 8901 (development code)        (858)+TX, cyantraniliprole [736994-63-19+TX, chlorantraniliprole        [500008-45-7]+TX, cyenopyrafen [560121-52-0]+TX, cyflumetofen        [400882-07-7]+TX, pyrifluquinazon [337458-27-2]+TX, spinetoram        [187166-40-1+187166-15-0]+TX, spirotetramat [203313-25-1]+TX,        sulfoxaflor [946578-00-3]+TX, flufiprole [704886-18-0]+TX,        meperfluthrin [915288-13-0]+TX, tetramethylfluthrin        [84937-88-2]+TX, triflumezopyrim (disclosed in WO        2012/092115)+TX,    -   a molluscicide selected from the group of substances consisting        of bis(tributyltin) oxide (IUPAC name) (913)+TX, bromoacetamide        [CCN]+TX, calcium arsenate [CCN]+TX, cloethocarb (999)+TX,        copper acetoarsenite [CCN]+TX, copper sulfate (172)+TX, fentin        (347)+TX, ferric phosphate (IUPAC name) (352)+TX, metaldehyde        (518)+TX, methiocarb (530)+TX, niclosamide (576)+TX,        niclosamide-olamine (576)+TX, pentachlorophenol (623)+TX, sodium        pentachlorophenoxide (623)+TX, tazimcarb (1412)+TX, thiodicarb        (799)+TX, tributyltin oxide (913)+TX, trifenmorph (1454)+TX,        trimethacarb (840)+TX, triphenyltin acetate (IUPAC name) (347)        and triphenyltin hydroxide (IUPAC name) (347)+TX, pyriprole        [394730-71-3]+TX,    -   a nematicide selected from the group of substances consisting of        AKD-3088 (compound code)+TX, 1,2-dibromo-3-chloropropane        (IUPAC/Chemical Abstracts name) (1045)+TX, 1,2-dichloropropane        (IUPAC/Chemical Abstracts name) (1062)+TX, 1,2-dichloropropane        with 1,3-dichloropropene (IUPAC name) (1063)+TX,        1,3-dichloropropene (233)+TX, 3,4-dichlorotetrahydrothiophene        1,1-dioxide (IUPAC/Chemical Abstracts name) (1065)+TX,        3-(4-chlorophenyl)-5-methylrhodanine (IUPAC name) (980)+TX,        5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid (IUPAC        name) (1286)+TX, 6-isopentenylaminopurine (alternative name)        (210)+TX, abamectin (1)+TX, acetoprole [CCN]+TX, alanycarb        (15)+TX, aldicarb (16)+TX, aldoxycarb (863)+TX, AZ 60541        (compound code)+TX, benclothiaz [CCN]+TX, benomyl (62)+TX,        butylpyridaben (alternative name)+TX, cadusafos (109)+TX,        carbofuran (118)+TX, carbon disulfide (945)+TX, carbosulfan        (119)+TX, chloropicrin (141)+TX, chlorpyrifos (145)+TX,        cloethocarb (999)+TX, cytokinins (alternative name) (210)+TX,        dazomet (216)+TX, DBCP (1045)+TX, DCIP (218)+TX, diamidafos        (1044)+TX, dichlofenthion (1051)+TX, dicliphos (alternative        name)+TX, dimethoate (262)+TX, doramectin (alternative name)        [CCN]+TX, emamectin (291)+TX, emamectin benzoate (291)+TX,        eprinomectin (alternative name) [CCN]+TX, ethoprophos (312)+TX,        ethylene dibromide (316)+TX, fenamiphos (326)+TX, fenpyrad        (alternative name)+TX, fensulfothion (1158)+TX, fosthiazate        (408)+TX, fosthietan (1196)+TX, furfural (alternative name)        [CCN]+TX, GY-81 (development code) (423)+TX, heterophos        [CCN]+TX, iodomethane (IUPAC name) (542)+TX, isamidofos        (1230)+TX, isazofos (1231)+TX, ivermectin (alternative name)        [CCN]+TX, kinetin (alternative name) (210)+TX, mecarphon        (1258)+TX, metam (519)+TX, metam-potassium (alternative name)        (519)+TX, metam-sodium (519)+TX, methyl bromide (537)+TX, methyl        isothiocyanate (543)+TX, milbemycin oxime (alternative name)        [CCN]+TX, moxidectin (alternative name) [CCN]+TX, Myrothecium        verrucaria composition (alternative name) (565)+TX, NC-184        (compound code)+TX, oxamyl (602)+TX, phorate (636)+TX,        phosphamidon (639)+TX, phosphocarb [CCN]+TX, sebufos        (alternative name)+TX, selamectin (alternative name) [CCN]+TX,        spinosad (737)+TX, terbam (alternative name)+TX, terbufos        (773)+TX, tetrachlorothiophene (IUPAC/Chemical Abstracts name)        (1422)+TX, thiafenox (alternative name)+TX, thionazin (1434)+TX,        triazophos (820)+TX, triazuron (alternative name)+TX, xylenols        [CCN]+TX, YI-5302 (compound code) and zeatin (alternative name)        (210)+TX, fluensulfone [318290-98-1]+TX,    -   a nitrification inhibitor selected from the group of substances        consisting of potassium ethylxanthate [CCN] and nitrapyrin        (580)+TX,    -   a plant activator selected from the group of substances        consisting of acibenzolar (6)+TX, acibenzolar-S-methyl (6)+TX,        probenazole (658) and Reynoutria sachalinensis extract        (alternative name) (720)+TX,    -   a rodenticide selected from the group of substances consisting        of 2-isovalerylindan-1,3-dione (IUPAC name) (1246)+TX,        4-(quinoxalin-2-ylamino)benzenesulfonamide (IUPAC name)        (748)+TX, alpha-chlorohydrin [CCN]+TX, aluminium phosphide        (640)+TX, antu (880)+TX, arsenous oxide (882)+TX, barium        carbonate (891)+TX, bisthiosemi (912)+TX, brodifacoum (89)+TX,        bromadiolone (91)+TX, bromethalin (92)+TX, calcium cyanide        (444)+TX, chloralose (127)+TX, chlorophacinone (140)+TX,        cholecalciferol (alternative name) (850)+TX, coumachlor        (1004)+TX, coumafuryl (1005)+TX, coumatetralyl (175)+TX,        crimidine (1009)+TX, difenacoum (246)+TX, difethialone (249)+TX,        diphacinone (273)+TX, ergocalciferol (301)+TX, flocoumafen        (357)+TX, fluoroacetamide (379)+TX, flupropadine (1183)+TX,        flupropadine hydrochloride (1183)+TX, gamma-HCH (430)+TX, HCH        (430)+TX, hydrogen cyanide (444)+TX, iodomethane (IUPAC name)        (542)+TX, lindane (430)+TX, magnesium phosphide (IUPAC name)        (640)+TX, methyl bromide (537)+TX, norbormide (1318)+TX,        phosacetim (1336)+TX, phosphine (IUPAC name) (640)+TX,        phosphorus [CCN]+TX, pindone (1341)+TX, potassium arsenite        [CCN]+TX, pyrinuron (1371)+TX, scilliroside (1390)+TX, sodium        arsenite [CCN]+TX, sodium cyanide (444)+TX, sodium fluoroacetate        (735)+TX, strychnine (745)+TX, thallium sulfate [CCN]+TX,        warfarin (851) and zinc phosphide (640)+TX,    -   a synergist selected from the group of substances consisting of        2-(2-butoxyethoxy)ethyl piperonylate (IUPAC name) (934)+TX,        5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone (IUPAC name)        (903)+TX, farnesol with nerolidol (alternative name) (324)+TX,        MB-599 (development code) (498)+TX, MGK 264 (development code)        (296)+TX, piperonyl butoxide (649)+TX, piprotal (1343)+TX,        propyl isomer (1358)+TX, S421 (development code) (724)+TX,        sesamex (1393)+TX, sesasmolin (1394) and sulfoxide (1406)+TX,    -   an animal repellent selected from the group of substances        consisting of anthraquinone (32)+TX, chloralose (127)+TX, copper        naphthenate [CCN]+TX, copper oxychloride (171)+TX, diazinon        (227)+TX, dicyclopentadiene (chemical name) (1069)+TX, guazatine        (422)+TX, guazatine acetates (422)+TX, methiocarb (530)+TX,        pyridin-4-amine (IUPAC name) (23)+TX, thiram (804)+TX,        trimethacarb (840)+TX, zinc naphthenate [CCN] and ziram        (856)+TX,    -   a virucide selected from the group of substances consisting of        imanin (alternative name) [CCN] and ribavirin (alternative name)        [CCN]+TX,    -   a wound protectant selected from the group of substances        consisting of mercuric oxide (512)+TX, octhilinone (590) and        thiophanate-methyl (802)+TX,    -   and biologically active compounds selected from the group        consisting of ametoctradin [865318-97-4]+TX, amisulbrom        [348635-87-0]+TX, azaconazole [60207-31-0]+TX, benzovindiflupyr        [1072957-71-1]+TX, bitertanol [70585-36-3]+TX, bixafen        [581809-46-3]+TX, bromuconazole [116255-48-2]+TX, coumoxystrobin        [850881-70-8]+TX, cyproconazole [94361-06-5]+TX, difenoconazole        [119446-68-3]+TX, diniconazole [83657-24-3]+TX, enoxastrobin        [238410-11-2]+TX, epoxiconazole [106325-08-0]+TX, fenbuconazole        [114369-43-6]+TX, fenpyrazamine [473798-59-3]+TX,        fluquinconazole [136426-54-5]+TX, flusilazole [85509-19-9]+TX,        flutriafol [76674-21-0]+TX, fluxapyroxad [907204-31-3]+TX,        fluopyram [658066-35-4]+TX, fenaminstrobin [366815-39-6]+TX,        isofetamid [875915-78-9]+TX, hexaconazole [79983-71-4]+TX,        imazalil [35554-44-0]+TX, imibenconazole [86598-92-7]+TX,        ipconazole [125225-28-7]+TX, ipfentrifluconazole        [1417782-08-1]+TX, isotianil [224049-04-1]+TX, mandestrobin        [173662-97-0] (can be prepared according to the procedures        described in WO 2010/093059)+TX, mefentrifluconazole        [1417782-03-6]+TX, metconazole [125116-23-6]+TX, myclobutanil        [88671-89-0]+TX, paclobutrazol [76738-62-0]+TX, pefurazoate        [101903-30-4]+TX, penflufen [494793-67-8]+TX, penconazole        [66246-88-6]+TX, prothioconazole [178928-70-6]+TX, pyrifenox        [88283-41-4]+TX, prochloraz [67747-09-5]+TX, propiconazole        [60207-90-1]+TX, simeconazole [149508-90-7]+TX, tebuconazole        [107534-96-3]+TX, tetraconazole [112281-77-3]+TX, triadimefon        [43121-43-3]+TX, triadimenol [55219-65-3]+TX, triflumizole        [99387-89-0]+TX, triticonazole [131983-72-7]+TX, ancymidol        [12771-68-5]+TX, fenarimol [60168-88-9]+TX, nuarimol        [63284-71-9]+TX, bupirimate [41483-43-6]+TX, dimethirimol        [5221-53-4]+TX, ethirimol [23947-60-6]+TX, dodemorph        [1593-77-7]+TX, fenpropidin [67306-00-7]+TX, fenpropimorph        [67564-91-4]+TX, spiroxamine [118134-30-8]+TX, tridemorph        [81412-43-3]+TX, cyprodinil [121552-61-2]+TX, mepanipyrim        [110235-47-7]+TX, pyrimethanil [53112-28-0]+TX, fenpiclonil        [74738-17-3]+TX, fludioxonil [131341-86-1]+TX, fluindapyr        [1383809-87-7]+TX, benalaxyl [71626-11-4]+TX, furalaxyl        [57646-30-7]+TX, metalaxyl [57837-19-1]+TX, R-metalaxyl        [70630-17-0]+TX, ofurace [58810-48-3]+TX, oxadixyl        [77732-09-3]+TX, benomyl [17804-35-2]+TX, carbendazim        [10605-21-7]+TX, debacarb [62732-91-6]+TX, fuberidazole        [3878-19-1]+TX, thiabendazole [148-79-8]+TX, chlozolinate        [84332-86-5]+TX, dichlozoline [24201-58-9]+TX, iprodione        [36734-19-7]+TX, myclozoline [54864-61-8]+TX, procymidone        [32809-16-8]+TX, vinclozoline [50471-44-8]+TX, boscalid        [188425-85-6]+TX, carboxin [5234-68-4]+TX, fenfuram        [24691-80-3]+TX, flutolanil [66332-96-5]+TX, flutianil        [958647-10-4]+TX, mepronil [55814-41-0]+TX, oxycarboxin        [5259-88-1]+TX, penthiopyrad [183675-82-3]+TX, thifluzamide        [130000-40-7]+TX, guazatine [108173-90-6]+TX, dodine [2439-10-3]        [112-65-2] (free base)+TX, iminoctadine [13516-27-3]+TX,        azoxystrobin [131860-33-8]+TX, dimoxystrobin [149961-52-4]+TX,        enestroburin {Proc. BCPC, Int. Congr., Glasgow, 2003, 1, 93}+TX,        fluoxastrobin [361377-29-9]+TX, kresoxim-methyl        [143390-89-0]+TX, metominostrobin [133408-50-1]+TX,        trifloxystrobin [141517-21-7]+TX, orysastrobin [248593-16-0]+TX,        picoxystrobin [117428-22-5]+TX, pyraclostrobin [175013-18-0]+TX,        pyraoxystrobin [862588-11-2]+TX, ferbam [14484-64-1]+TX,        mancozeb [8018-01-7]+TX, maneb [12427-38-2]+TX, metiram        [9006-42-2]+TX, propineb [12071-83-9]+TX, thiram [137-26-8]+TX,        zineb [12122-67-7]+TX, ziram [137-30-4]+TX, captafol        [2425-06-1]+TX, captan [133-06-2]+TX, dichlofluanid        [1085-98-9]+TX, fluoroimide [41205-21-4]+TX, folpet        [133-07-3]+TX, tolylfluanid [731-27-1]+TX, bordeaux mixture        [8011-63-0]+TX, copperhydroxid [20427-59-2]+TX, copperoxychlorid        [1332-40-7]+TX, coppersulfat [7758-98-7]+TX, copperoxid        [1317-39-1]+TX, mancopper [53988-93-5]+TX, oxine-copper        [10380-28-6]+TX, dinocap [131-72-6]+TX, nitrothal-isopropyl        [10552-74-6]+TX, edifenphos [17109-49-8]+TX, iprobenphos        [26087-47-8]+TX, isoprothiolane [50512-35-1]+TX, phosdiphen        [36519-00-3]+TX, pyrazophos [13457-18-6]+TX, tolclofos-methyl        [57018-04-9]+TX, acibenzolar-S-methyl [135158-54-2]+TX,        anilazine [101-05-3]+TX, benthiavalicarb [413615-35-7]+TX,        blasticidin-S [2079-00-7]+TX, chinomethionat [2439-01-2]+TX,        chloroneb [2675-77-6]+TX, chlorothalonil [1897-45-6]+TX,        cyflufenamid [180409-60-3]+TX, cymoxanil [57966-95-7]+TX,        dichlone [117-80-6]+TX, diclocymet [139920-32-4]+TX, diclomezine        [62865-36-5]+TX, dicloran [99-30-9]+TX, diethofencarb        [87130-20-9]+TX, dimethomorph [110488-70-5]+TX, SYP-LI90        (Flumorph) [211867-47-9]+TX, dithianon [3347-22-6]+TX, ethaboxam        [162650-77-3]+TX, etridiazole [2593-15-9]+TX, famoxadone        [131807-57-3]+TX, fenamidone [161326-34-7]+TX, fenoxanil        [115852-48-7]+TX, fentin [668-34-8]+TX, ferimzone        [89269-64-7]+TX, fluazinam [79622-59-6]+TX, fluopicolide        [239110-15-7]+TX, flusulfamide [106917-52-6]+TX, fenhexamid        [126833-17-8]+TX, fosetyl-aluminium [39148-24-8]+TX, hymexazol        [10004-44-1]+TX, iprovalicarb [140923-17-7]+TX, IKF-916        (Cyazofamid) [120116-88-3]+TX, kasugamycin [6980-18-3]+TX,        methasulfocarb [66952-49-6]+TX, metrafenone [220899-03-6]+TX,        pencycuron [66063-05-6]+TX, phthalide [27355-22-2]+TX,        picarbutrazox [500207-04-5]+TX, polyoxins [11113-80-7]+TX,        probenazole [27605-76-1]+TX, propamocarb [25606-41-1]+TX,        proquinazid [189278-12-4]+TX, pydiflumetofen [1228284-64-7]+TX,        pyrametostrobin [915410-70-7]+TX, pyroquilon [57369-32-1]+TX,        pyriofenone [688046-61-9]+TX, pyribencarb [799247-52-2]+TX,        pyrisoxazole [847749-37-5]+TX, quinoxyfen [124495-18-7]+TX,        quintozene [82-68-8]+TX, sulfur [7704-34-9]+TX, Timorex Gold™        (plant extract containing tea tree oil from the Stockton        Group)+TX, tebufloquin [376645-78-2]+TX, tiadinil        [223580-51-6]+TX, triazoxide [72459-58-6]+TX, tolprocarb        [911499-62-2]+TX, triclopyricarb [902760-40-1]+TX, tricyclazole        [41814-78-2]+TX, triforine [26644-46-2]+TX, validamycin        [37248-47-8]+TX, valifenalate [283159-90-0]+TX, zoxamide        (RH7281) [156052-68-5]+TX, mandipropamid [374726-62-2]+TX,        isopyrazam [881685-58-1]+TX, phenamacril+TX, sedaxane        [874967-67-6]+TX, trinexapac-ethyl [95266-40-3]+TX,        3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid        (9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide        (dislosed in WO 2007/048556)+TX,        3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid        (3′,4′,5′-trifluoro-biphenyl-2-yl)-amide (disclosed in WO        2006/087343)+TX,        [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(cyclopropylcarbonyl)oxy]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-6,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,        11        Hnaphtho[2,1-b]pyrano[3,4-e]pyran-4-yl]methyl-cyclopropanecarboxylate        [915972-17-7]+TX and        1,3,5-trimethyl-N-(2-methyl-1-oxopropyl)-N-[3-(2-methylpropyl)-4-[2,2,2-trifluoro-1-methoxy-1-(trifluoromethyl)ethyl]phenyl]-1H-pyrazole-4-carboxamide        [926914-55-8]+TX,    -   or a biologically active compound selected from the group        consisting of        N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide        (can be prepared according to the procedures described in WO        2010/130767)+TX,        2,6-Dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone        (can be prepared according to the procedures described in WO        2011/138281)+TX,        6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile+TX,        4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazazol-3-amine        (can be prepared according to the procedures described in WO        2012/031061)+TX,        3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide        (can be prepared according to the procedures described in WO        2012/084812)+TX, CAS 850881-30-0+TX,        3-(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,2-benzothiazole        1,1-dioxide (can be prepared according to the procedures        described in WO 2007/129454)+TX,        2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxy-N-methyl-acetamide+TX,        3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone        (can be prepared according to the procedures described in WO        2005/070917)+TX,        2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol        (can be prepared according to the procedures described in WO        2011/081174)+TX,        2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol        (can be prepared according to the procedures described in WO        2011/081174)+TX, oxathiapiprolin+TX [1003318-67-9], tert-butyl        N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate+TX,        N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide        (can be prepared according to the procedures described in WO        2007/072999)+TX,        3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide        (can be prepared according to the procedures described in WO        2014/013842)+TX, 2,2,2-trifluoroethyl        N-[2-methyl-1-[[(4-methylbenzoyl)amino]methyl]propyl]carbamate+TX,        (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol+TX,        (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol+TX,        2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide+TX,        2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide+TX,        N′-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine+TX,        N′-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine        (can be prepared according to the procedures described in WO        2007/031513)+TX,        [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]        methanesulfonate (can be prepared according to the procedures        described in WO 2012/025557)+TX, but-3-ynyl        N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate        (can be prepared according to the procedures described in WO        2010/000841)+TX,        2-[[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl]-4H-1,2,4-triazole-3-thione        (can be prepared according to the procedures described in WO        2010/146031)+TX, methyl        N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate+TX,        3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine        (can be prepared according to the procedures described in WO        2005/121104)+TX,        2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol        (can be prepared according to the procedures described in WO        2013/024082)+TX,        3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine        (can be prepared according to the procedures described in WO        2012/020774)+TX,        4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile        (can be prepared according to the procedures described in WO        2012/020774)+TX,        (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide        (can be prepared according to the procedures described in WO        2011/162397)+TX,        3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide        (can be prepared according to the procedures described in WO        2012/084812)+TX,        1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one        (can be prepared according to the procedures described in WO        2013/162072)+TX,        1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one        (can be prepared according to the procedures described in WO        2014/051165)+TX,        (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide+TX,        (4-phenoxyphenyl)methyl        2-amino-6-methyl-pyridine-3-carboxylate+TX,        N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide        [1255734-28-1] (can be prepared according to the procedures        described in WO 2010/130767)+TX,        3-(difluoromethyl)-N—[(R)-2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methylpyrazole-4-carboxamide        [1352994-67-2]+TX,        N′-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine+TX,        N′-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine+TX,        N′-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine+TX,        N′-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine+TX,

(fenpicoxamid [517875-34-2])+TX (as described in WO 2003/035617),2-(difluoromethyl)-N-(1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide+TX,2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide+TX,2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide+TX,2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide+TX,2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide+TX,2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide+TX,and2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide+TX,wherein each of these carboxamide compounds can be prepared according tothe procedures described in WO 2014/095675 and/or WO 2016/139189.

The references in brackets behind the active ingredients, e.g.[3878-19-1] refer to the Chemical Abstracts Registry number. The abovedescribed mixing partners are known. Where the active ingredients areincluded in “The Pesticide Manual” [The Pesticide Manual—A WorldCompendium; Thirteenth Edition; Editor: C. D. S. TomLin; The BritishCrop Protection Council], they are described therein under the entrynumber given in round brackets hereinabove for the particular compound;for example, the compound “abamectin” is described under entry number(1). Where “[CCN]” is added hereinabove to the particular compound, thecompound in question is included in the “Compendium of Pesticide CommonNames”, which is accessible on the internet [A. Wood; Compendium ofPesticide Common Names, Copyright © 1995-2004]; for example, thecompound “acetoprole” is described under the internet addresshttp://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are referred tohereinabove by a so-called “common name”, the relevant “ISO common name”or another “common name” being used in individual cases. If thedesignation is not a “common name”, the nature of the designation usedinstead is given in round brackets for the particular compound; in thatcase, the IUPAC name, the IUPAC/Chemical Abstracts name, a “chemicalname”, a “traditional name”, a “compound name” or a “develoment code” isused or, if neither one of those designations nor a “common name” isused, an “alternative name” is employed. “CAS Reg. No” means theChemical Abstracts Registry Number.

The active ingredient mixture of a compound of Formula (I) as describedin Table 1 (a compound of Formulae (1.a) to (1.ah)) or a compound ofFormula (I) described in Table 2 (below) and another active ingredientas described above are preferably in a mixing ratio of from 100:1 to1:6000, especially from 50:1 to 1:50, more especially in a ratio of from20:1 to 1:20, even more especially from 10:1 to 1:10, very especiallyfrom 5:1 and 1:5, special preference being given to a ratio of from 2:1to 1:2, and a ratio of from 4:1 to 2:1 being likewise preferred, aboveall in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2,or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4,or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000,or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750.Those mixing ratios are by weight.

The mixtures as described above can be used in a method for controllingpests, which comprises applying a composition comprising a mixture asdescribed above to the pests or their environment, with the exception ofa method for treatment of the human or animal body by surgery or therapyand diagnostic methods practised on the human or animal body.

The mixtures comprising a compound of Formula (I) as described in Table1 (a compound of Formulae (1.a) to (1.ah)) or a compound of Formula (I)described in Table 2 (below), and one or more active ingredients asdescribed above can be applied, for example, in a single “ready-mix”form, in a combined spray mixture composed from separate formulations ofthe single active ingredient components, such as a “tank-mix”, and in acombined use of the single active ingredients when applied in asequential manner, i.e. one after the other with a reasonably shortperiod, such as a few hours or days. The order of applying the compoundof Formula (I) as described in Table 1 (a compound of Formulae (1.a) to(1.ah)) or a compound of Formula (I) described in Table 2 (below) andthe active ingredient(s) as described above, is not essential forworking the present invention.

The compositions according to the invention can also comprise furthersolid or liquid auxiliaries, such as stabilizers, for exampleunepoxidized or epoxidized vegetable oils (for example epoxidizedcoconut oil, rapeseed oil or soya oil), antifoams, for example siliconeoil, preservatives, viscosity regulators, binders and/or tackifiers,fertilizers or other active ingredients for achieving specific effects,for example bactericides, fungicides, nematocides, plant activators,molluscicides or herbicides.

The compositions according to the invention are prepared in a mannerknown per se, in the absence of auxiliaries for example by grinding,screening and/or compressing a solid active ingredient and in thepresence of at least one auxiliary for example by intimately mixingand/or grinding the active ingredient with the auxiliary (auxiliaries).These processes for the preparation of the compositions and the use ofthe compounds of Formula (I) for the preparation of these compositionsare also a subject of the invention.

Another aspect of invention is related to the use of a compound offormula (I) or of a preferred individual compound as above-defined, of acomposition comprising at least one compound of formula (I) or at leastone preferred individual compound as above-defined, or of a fungicidalor insecticidal mixture comprising at least one compound of formula (I)or at least one preferred individual compound as above-defined, inadmixture with other fungicides or insecticides as described above, forcontrolling or preventing infestation of plants, e.g. useful plants suchas crop plants, propagation material thereof, e.g. seeds, harvestedcrops, e.g., harvested food crops, or non-living materials by insects orby phytopathogenic microorganisms, preferably fungal organisms.

A further aspect of invention is related to a method of controlling orpreventing an infestation of plants, e.g., useful plants such as cropplants, propagation material thereof, e.g. seeds, harvested crops, e.g.harvested food crops, or of non-living materials by insects or byphytopathogenic or spoilage microorganisms or organisms potentiallyharmful to man, especially fungal organisms, which comprises theapplication of a compound of formula (I) or of a preferred individualcompound as above-defined as active ingredient to the plants, to partsof the plants or to the locus thereof, to the propagation materialthereof, or to any part of the non-living materials.

Controlling or preventing means reducing infestation by insects or byphytopathogenic or spoilage microorganisms or organisms potentiallyharmful to man, especially fungal organisms, to such a level that animprovement is demonstrated.

A preferred method of controlling or preventing an infestation of cropplants by phytopathogenic microorganisms, especially fungal organisms,or insects which comprises the application of a compound of formula (I),or an agrochemical composition which contains at least one of saidcompounds, is foliar application. The frequency of application and therate of application will depend on the risk of infestation by thecorresponding pathogen or insect. However, the compounds of formula (I)can also penetrate the plant through the roots via the soil (systemicaction) by drenching the locus of the plant with a liquid formulation,or by applying the compounds in solid form to the soil, e.g., ingranular form (soil application). In crops of water rice such granulatescan be applied to the flooded rice field. The compounds of formula (I)may also be applied to seeds (coating) by impregnating the seeds ortubers either with a liquid formulation of the fungicide or coating themwith a solid formulation.

A formulation, e.g. a composition containing the compound of formula(I), and, if desired, a solid or liquid adjuvant or monomers forencapsulating the compound of formula (I), may be prepared in a knownmanner, typically by intimately mixing and/or grinding the compound withextenders, for example solvents, solid carriers and, optionally, surfaceactive compounds (surfactants).

Advantageous rates of application are normally from 5 g to 2 kg ofactive ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kga.i./ha, most preferably from 20 g to 600 g a.i./ha. When used as seeddrenching agent, convenient dosages are from 10 mg to 1 g of activesubstance per kg of seeds.

When the combinations of the present invention are used for treatingseed, rates of 0.001 to 50 g of a compound of formula (I) per kg ofseed, preferably from 0.01 to 10 g per kg of seed are generallysufficient.

The compositions of the invention may be employed in any conventionalform, for example in the form of a twin pack, a powder for dry seedtreatment (DS), an emulsion for seed treatment (ES), a flowableconcentrate for seed treatment (FS), a solution for seed treatment (LS),a water dispersible powder for seed treatment (WS), a capsule suspensionfor seed treatment (CF), a gel for seed treatment (GF), an emulsionconcentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE),a capsule suspension (CS), a water dispersible granule (WG), anemulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion,oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oilmiscible flowable (OF), an oil miscible liquid (OL), a solubleconcentrate (SL), an ultra-low volume suspension (SU), an ultra-lowvolume liquid (UL), a technical concentrate (TK), a dispersibleconcentrate (DC), a wettable powder (WP) or any technically feasibleformulation in combination with agriculturally acceptable adjuvants.

Such compositions may be produced in conventional manner, e.g., bymixing the active ingredients with appropriate formulation inerts(diluents, solvents, fillers and optionally other formulatingingredients such as surfactants, biocides, anti-freeze, stickers,thickeners and compounds that provide adjuvancy effects). Alsoconventional slow release formulations may be employed where longlasting efficacy is intended. Particularly formulations to be applied inspraying forms, such as water dispersible concentrates (e.g. EC, SC, DC,OD, SE, EW, EO and the like), wettable powders and granules, may containsurfactants such as wetting and dispersing agents and other compoundsthat provide adjuvancy effects, e.g. the condensation product offormaldehyde with naphthalene sulphonate, an alkylarylsulphonate, alignin sulphonate, a fatty alkyl sulphate, and ethoxylated alkylphenoland an ethoxylated fatty alcohol.

A seed dressing formulation is applied in a manner known per se to theseeds employing the combination of the invention and a diluent insuitable seed dressing formulation form, e.g., as an aqueous suspensionor in a dry powder form having good adherence to the seeds. Such seeddressing formulations are known in the art. Seed dressing formulationsmay contain the single active ingredients or the combination of activeingredients in encapsulated form, e.g. as slow release capsules ormicrocapsules.

In general, the formulations include from 0.01 to 90% by weight ofactive agent, from 0 to 20% agriculturally acceptable surfactant and 10to 99.99% solid or liquid formulation inerts and adjuvant(s), the activeagent consisting of at least the compound of formula (I) together withcomponent (B) and (C), and optionally other active agents, particularlymicrobiocides or conservatives or the like. Concentrated forms ofcompositions generally contain in between about 2 and 80%, preferablybetween about 5 and 70% by weight of active agent. Application forms offormulation may for example contain from 0.01 to 20% by weight,preferably from 0.01 to 5% by weight of active agent. Whereas commercialproducts will preferably be formulated as concentrates, the end userwill normally employ diluted formulations.

TABLE 1 Examples of individual compounds of formula (I) according to theinvention. Compound No. R¹ R² R⁴ R⁵ R⁶ R⁷ 001 CH₃ OH CH₃ CH₃ CH₃ CH₃ 002CH₃ OH CH₃ CH₃ CH₃ CH₂CH₃ 003 CH₃ OH CH₃ CH₃ CH₂CH₃ CH₂CH₃ 004 CH₃ OHCH₃ CH₃ CH₃ CH(CH₃)₂ 005 CH₃ OH CH₃ CH₃ CH₃ cyclopropyl 006 CH₃ OH CH₃CH₃ —CH₂CH₂— 007 CH₃ OH CH₃ CH₃ —CH₂CH₂— 008 CH₃ OH CH₃ CH₃—CH(CH(CH₃)₂)CH₂— 009 CH₃ OH CH₃ CH₃ —CH(cyclopropyl)CH₂— 010 CH₃ OH CH₃CH₃ —CH(Ph)CH₂— 011 CH₃ OH CH₃ CH₃ —CH(4-F—Ph)CH₂— 012 CH₃ OH CH₃ CH₃—CH₂CH₂CH₂— 013 CH₃ OH CH₃ CH₃ —CH₂CH(Ph)CH₂— 014 CH₃ OH CH₃ CH₃—CH₂CH₂CH₂CH₂— 015 CH₃ OH CH₃ CH₃ —CH₂CH₂CH₂CH₂CH₂— 016 CH₃ OH CH₃CH₂CH₃ CH₃ CH₃ 017 CH₃ OH CH₃ CH₂CH₃ CH₃ CH₂CH₃ 018 CH₃ OH CH₃ CH₂CH₃CH₂CH₃ CH₂CH₃ 019 CH₃ OH CH₃ CH₂CH₃ CH₃ CH(CH₃)₂ 020 CH₃ OH CH₃ CH₂CH₃CH₃ cyclopropyl 021 CH₃ OH CH₃ CH₂CH₃ —CH₂CH₂— 022 CH₃ OH CH₃ CH₂CH₃—CH₂CH₂— 023 CH₃ OH CH₃ CH₂CH₃ —CH(CH(CH₃)₂)CH₂— 024 CH₃ OH CH₃ CH₂CH₃—CH(cyclopropyl)CH₂— 025 CH₃ OH CH₃ CH₂CH₃ —CH(Ph)CH₂— 026 CH₃ OH CH₃CH₂CH₃ —CH(4-F—Ph)CH₂— 027 CH₃ OH CH₃ CH₂CH₃ —CH₂CH₂CH₂— 028 CH₃ OH CH₃CH₂CH₃ —CH₂CH(Ph)CH₂— 029 CH₃ OH CH₃ CH₂CH₃ —CH₂CH₂CH₂CH₂— 030 CH₃ OHCH₃ CH₂CH₃ —CH₂CH₂CH₂CH₂CH₂— 031 CH₃ OH CH₂CH₃ CH₃ CH₃ CH₃ 032 CH₃ OHCH₂CH₃ CH₃ CH₃ CH₂CH₃ 033 CH₃ OH CH₂CH₃ CH₃ CH₂CH₃ CH₂CH₃ 034 CH₃ OHCH₂CH₃ CH₃ CH₃ CH(CH₃)₂ 035 CH₃ OH CH₂CH₃ CH₃ CH₃ cyclopropyl 036 CH₃ OHCH₂CH₃ CH₃ —CH₂CH₂— 037 CH₃ OH CH₂CH₃ CH₃ —CH₂CH₂— 038 CH₃ OH CH₂CH₃ CH₃—CH(CH(CH₃)₂)CH₂— 039 CH₃ OH CH₂CH₃ CH₃ —CH(cyclopropyl)CH₂— 040 CH₃ OHCH₂CH₃ CH₃ —CH(Ph)CH₂— 041 CH₃ OH CH₂CH₃ CH₃ —CH(4-F—Ph)CH₂— 042 CH₃ OHCH₂CH₃ CH₃ —CH₂CH₂CH₂— 043 CH₃ OH CH₂CH₃ CH₃ —CH₂CH(Ph)CH₂— 044 CH₃ OHCH₂CH₃ CH₃ —CH₂CH₂CH₂CH₂— 045 CH₃ OH CH₂CH₃ CH₃ —CH₂CH₂CH₂CH₂CH₂— 046CH₃ OH CH₃ CH₃ CH₃ CH₃ 047 CH₃ OH CH₃ CH₃ CH₃ CH₂CH₃ 048 CH₃ OH CH₃ CH₃CH₂CH₃ CH₂CH₃ 049 CH₃ OH CH₃ CH₃ CH₃ CH(CH₃)₂ 050 CH₃ OH CH₃ CH₃ CH₃cyclopropyl 051 CH₃ OH CH₃ CH₃ —CH₂CH₂— 052 CH₃ OH CH₃ CH₃ —CH₂CH₂— 053CH₃ OH CH₃ CH₃ —CH(CH(CH₃)₂)CH₂— 054 CH₃ OH CH₃ CH₃ —CH(cyclopropyl)CH₂—055 CH₃ OH CH₃ CH₃ —CH(Ph)CH₂— 056 CH₃ OH CH₃ CH₃ —CH(4-F—Ph)CH₂— 057CH₃ OH CH₃ CH₃ —CH₂CH₂CH₂— 058 CH₃ OH CH₃ CH₃ —CH₂CH(Ph)CH₂— 059 CH₃ OHCH₃ CH₃ —CH₂CH₂CH₂CH₂— 060 CH₃ OH CH₃ CH₃ —CH₂CH₂CH₂CH₂CH₂— 061 CH₃OC(═O)CH₃ CH₃ CH₃ CH₃ CH₃ 062 CH₃ OC(═O)CH₃ CH₃ CH₃ CH₃ CH₂CH₃ 063 CH₃OC(═O)CH₃ CH₃ CH₃ CH₂CH₃ CH₂CH₃ 064 CH₃ OC(═O)CH₃ CH₃ CH₃ CH₃ CH(CH₃)₂065 CH₃ OC(═O)CH₃ CH₃ CH₃ CH₃ cyclopropyl 066 CH₃ OC(═O)CH₃ CH₃ CH₃—CH₂CH₂— 067 CH₃ OC(═O)CH₃ CH₃ CH₃ —CH₂CH₂— 068 CH₃ OC(═O)CH₃ CH₃ CH₃—CH(CH(CH₃)₂)CH₂— 069 CH₃ OC(═O)CH₃ CH₃ CH₃ —CH(cyclopropyl)CH₂— 070 CH₃OC(═O)CH₃ CH₃ CH₃ —CH(Ph)CH₂— 071 CH₃ OC(═O)CH₃ CH₃ CH₃ —CH(4-F—Ph)CH₂—072 CH₃ OC(═O)CH₃ CH₃ CH₃ —CH₂CH₂CH₂— 073 CH₃ OC(═O)CH₃ CH₃ CH₃—CH₂CH(Ph)CH₂— 074 CH₃ OC(═O)CH₃ CH₃ CH₃ —CH₂CH₂CH₂CH₂— 075 CH₃OC(═O)CH₃ CH₃ CH₃ —CH₂CH₂CH₂CH₂CH₂— 076 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃ CH₃ CH₃077 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃ CH₃ CH₂CH₃ 078 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃CH₂CH₃ CH₂CH₃ 079 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃ CH₃ CH(CH₃)₂ 080 CH₃OC(═O)CH₂CH₃ CH₃ CH₃ CH₃ cyclopropyl 081 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃—CH₂CH₂— 082 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃ —CH₂CH₂— 083 CH₃ OC(═O)CH₂CH₃ CH₃CH₃ —CH(CH(CH₃)₂)CH₂— 084 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃ —CH(cyclopropyl)CH₂—085 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃ —CH(Ph)CH₂— 086 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃—CH(4-F—Ph)CH₂— 087 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃ —CH₂CH₂CH₂— 088 CH₃OC(═O)CH₂CH₃ CH₃ CH₃ —CH₂CH(Ph)CH₂— 089 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃—CH₂CH₂CH₂CH₂— 090 CH₃ OC(═O)CH₂CH₃ CH₃ CH₃ —CH₂CH₂CH₂CH₂CH₂— 091 CH₃OCH₂OC(═O)CH₃ CH₃ CH₃ CH₃ CH₃ 092 CH₃ OCH₂OC(═O)CH₃ CH₃ CH₃ CH₃ CH₂CH₃093 CH₃ OCH₂OC(═O)CH₃ CH₃ CH₃ CH₂CH₃ CH₂CH₃ 094 CH₃ OCH₂OC(═O)CH₃ CH₃CH₃ CH₃ CH(CH₃)₂ 095 CH₃ OCH₂OC(═O)CH₃ CH₃ CH₃ CH₃ cyclopropyl 096 CH₃OCH₂OC(═O)CH₃ CH₃ CH₃ —CH₂CH₂— 097 CH₃ OCH₂OC(═O)CH₃ CH₃ CH₃ —CH₂CH₂—098 CH₃ OCH₂OC(═O)CH₃ CH₃ CH₃ —CH(CH(CH₃)₂)CH₂— 099 CH₃ OCH₂OC(═O)CH₃CH₃ CH₃ —CH(cyclopropyl)CH₂— 100 CH₃ OCH₂OC(═O)CH₃ CH₃ CH₃ —CH(Ph)CH₂—101 CH₃ OCH₂OC(═O)CH₃ CH₃ CH₃ —CH(4-F—Ph)CH₂— 102 CH₃ OCH₂OC(═O)CH₃ CH₃CH₃ —CH₂CH₂CH₂— 103 CH₃ OCH₂OC(═O)CH₃ CH₃ CH₃ —CH₂CH(Ph)CH₂— 104 CH₃OCH₂OC(═O)CH₃ CH₃ CH₃ —CH₂CH₂CH₂CH₂— 105 CH₃ OCH₂OC(═O)CH₃ CH₃ CH₃—CH₂CH₂CH₂CH₂CH₂— 106 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ CH₃ CH₃ 107 CH₃OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ CH₃ CH₂CH₃ 108 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃CH₂CH₃ CH₂CH₃ 109 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ CH₃ CH(CH₃)₂ 110 CH₃OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ CH₃ cyclopropyl 111 CH₃ OCH₂OC(═O)CH(CH₃)₂CH₃ CH₃ —CH₂CH₂— 112 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ —CH₂CH₂— 113 CH₃OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ —CH(CH(CH₃)₂)CH₂— 114 CH₃ OCH₂OC(═O)CH(CH₃)₂CH₃ CH₃ —CH(cyclopropyl)CH₂— 115 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃—CH(Ph)CH₂— 116 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ —CH(4-F—Ph)CH₂— 117 CH₃OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ —CH₂CH₂CH₂— 118 CH₃ OCH₂OC(═O)CH₂CH₃ CH₃ CH₃—CH₂CH(Ph)CH₂— 119 CH₃ OCH₂OC(═O)CH₂CH₃ CH₃ CH₃ —CH₂CH₂CH₂CH₂— 120 CH₃OCH₂OC(═O)CH₂CH₃ CH₃ CH₃ —CH₂CH₂CH₂CH₂CH₂— 121 CH₃ OCH₂OC(═O)CH(CH₃)₂CH₃ CH₃ CH₃ CH₃ 122 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ CH₃ CH₂CH₃ 123 CH₃OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ CH₂CH₃ CH₂CH₃ 124 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃CH₃ CH₃ CH(CH₃)₂ 125 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ CH₃ cyclopropyl 126CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ —CH₂CH₂— 127 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃CH₃ —CH₂CH₂— 128 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ —CH(CH(CH₃)₂)CH₂— 129CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ —CH(cyclopropyl)CH₂— 130 CH₃OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ —CH(Ph)CH₂— 131 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃CH₃ —CH(4-F—Ph)CH₂— 132 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ —CH₂CH₂CH₂— 133CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃ —CH₂CH(Ph)CH₂— 134 CH₃ OCH₂OC(═O)CH(CH₃)₂CH₃ CH₃ —CH₂CH₂CH₂CH₂— 135 CH₃ OCH₂OC(═O)CH(CH₃)₂ CH₃ CH₃—CH₂CH₂CH₂CH₂CH₂— 136 CH₂CH₃ OH CH₃ CH₃ CH₃ CH₃ 137 CH₂CH₃ OH CH₃ CH₃CH₃ CH₂CH₃ 138 CH₂CH₃ OH CH₃ CH₃ CH₂CH₃ CH₂CH₃ 139 CH₂CH₃ OH CH₃ CH₃ CH₃CH(CH₃)₂ 140 CH₂CH₃ OH CH₃ CH₃ CH₃ cyclopropyl 141 CH₂CH₃ OH CH₃ CH₃—CH₂CH₂— 142 CH₂CH₃ OH CH₃ CH₃ —CH₂CH₂— 143 CH₂CH₃ OH CH₃ CH₃—CH(CH(CH₃)₂)CH₂— 144 CH₂CH₃ OH CH₃ CH₃ —CH(cyclopropyl)CH₂— 145 CH₂CH₃OH CH₃ CH₃ —CH(Ph)CH₂— 146 CH₂CH₃ OH CH₃ CH₃ —CH(4-F—Ph)CH₂— 147 CH₂CH₃OH CH₃ CH₃ —CH₂CH₂CH₂— 148 CH₂CH₃ OH CH₃ CH₃ —CH₂CH(Ph)CH₂— 149 CH₂CH₃OH CH₃ CH₃ —CH₂CH₂CH₂CH₂— 150 CH₂CH₃ OH CH₃ CH₃ —CH₂CH₂CH₂CH₂CH₂—Wherein there are:a) 150 compounds of formula (I.a):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.b) 150 compounds of formula (I.b):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.c) 150 compounds of formula (I.c):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.d) 150 compounds of formula (I.d):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.e) 150 compounds of formula (I.e):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.f) 150 compounds of formula (I.f):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.g) 150 compounds of formula (I.g):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.h) 150 compounds of formula (I.h):

Wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.i) 150 compounds of formula (I.i):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.j) 150 compounds of formula (I.j):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.k) 150 compounds of formula (I.k):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.m) 150 compounds of formula (I.m):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.n) 150 compounds of formula (I.n):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.o) 150 compounds of formula (I.o):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.p) 150 compounds of formula (I.p):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.q) 150 compounds of formula (I.q):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.r) 150 compounds of formula (I.r):

Wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.s) 150 compounds of formula (I.s):

Wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.t) 150 compounds of formula (I.t):

Wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.u) 150 compounds of formula (I.u):

Wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.v) 150 compounds of formula (I.v):

Wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.w) 150 compounds of formula (I.w):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.x) 150 compounds of formula (I.x):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.y) 150 compounds of formula (I.y):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Tablez) 150 compounds of formula (I.z):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.aa) 150 compounds of formula (I.aa):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.ab) 150 compounds of formula (I.ab):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.ac) 150 compounds of formula (I.ac):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.ad) 150 compounds of formula (I.ad):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.ae) 150 compounds of formula (I.ae):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.af) 150 compounds of formula (I.af):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.ag) 150 compounds of formula (I.ag):

wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.ah) 150 compounds of formula (I.ah):

Wherein R¹, R², R⁴, R⁵, R⁶ and R⁷ are as defined in Table 1.

FORMULATION EXAMPLES Wettable Powders a) b) c)

a) b) c) active ingredient [compound of formula (I)] 25%  50% 75% sodiumlignosulfonate 5%  5% — sodium lauryl sulfate 3% —  5% sodiumdiisobutylnaphthalenesulfonate —  6% 10% phenol polyethylene glycolether —  2% — (7-8 mol of ethylene oxide) highly dispersed silicic acid5% 10% 10% Kaolin 62%  27% —

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders that can be diluted with water to give suspensions of thedesired concentration.

Powders for Dry Seed Treatment a) b) c)

a) b) c) active ingredient [compound of formula (I)] 25% 50% 75% lightmineral oil  5%  5%  5% highly dispersed silicic acid  5%  5% — Kaolin65% 40% — Talcum — 20%

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording powders thatcan be used directly for seed treatment.

Emulsifiable Concentrate

active ingredient [compound of formula (I)] 10% octylphenol polyethyleneglycol ether  3% (4-5 mol of ethylene oxide) calciumdodecylbenzenesulfonate  3% castor oil polyglycol ether (35 mol ofethylene oxide)  4% Cyclohexanone 30% xylene mixture 50%Emulsions of any required dilution, which can be used in plantprotection, can be obtained from this concentrate by dilution withwater.

Dusts a) b) c)

a) b) c) Active ingredient [compound of formula (I)]  5%  6%  4% talcum95% — — Kaolin — 94% — mineral filler — — 96%

Ready-for-use dusts are obtained by mixing the active ingredient withthe carrier and grinding the mixture in a suitable mill. Such powderscan also be used for dry dressings for seed.

Extruder Granules

Active ingredient [compound of formula (I)] 15% sodium lignosulfonate 2% carboxymethylcellulose  1% Kaolin 82%

The active ingredient is mixed and ground with the adjuvants, and themixture is moistened with water. The mixture is extruded and then driedin a stream of air.

Coated Granules

Active ingredient [compound of formula (I)] 8% polyethylene glycol (mol.wt. 200) 3% Kaolin 89% 

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coated granulesare obtained in this manner.

Suspension Concentrate

active ingredient [compound of formula (I)] 40% propylene glycol 10%nonylphenol polyethylene glycol ether (15 mol of ethylene oxide)  6%Sodium lignosulfonate 10% carboxymethylcellulose  1% silicone oil (inthe form of a 75% emulsion in water)  1% Water 32%

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

Flowable concentrate for seed treatment

active ingredient [compound of formula (I)] 40%  propylene glycol 5%copolymer butanol PO/EO 2% tristyrenephenole with 10-20 moles EO 2%1,2-benzisothiazolin-3-one 0.5%  (in the form of a 20% solution inwater) monoazo-pigment calcium salt 5% Silicone oil (in the form of a75% emulsion in water) 0.2%  Water 45.3%  

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

Slow Release Capsule Suspension

28 parts of a combination of the compound of formula (I) are mixed with2 parts of an aromatic solvent and 7 parts of toluenediisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). Thismixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol,0.05 parts of a defoamer and 51.6 parts of water until the desiredparticle size is achieved. To this emulsion a mixture of 2.8 parts1,6-diaminohexane in 5.3 parts of water is added. The mixture isagitated until the polymerization reaction is completed.

The obtained capsule suspension is stabilized by adding 0.25 parts of athickener and 3 parts of a dispersing agent. The capsule suspensionformulation contains 28% of the active ingredients. The medium capsulediameter is 8-15 microns.

The resulting formulation is applied to seeds as an aqueous suspensionin an apparatus suitable for that purpose.

Examples

The Examples which follow serve to illustrate the invention.

The compounds of the invention can be distinguished from known compoundsby virtue of greater efficacy at low application rates, which can beverified by the person skilled in the art using the experimentalprocedures outlined in the Examples, using lower application rates ifnecessary, for example 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppmor 0.2 ppm.

Compounds of formula (I) may possess any number of benefits including,inter alia, advantageous levels of biological activity for protectingplants against diseases that are caused by fungi or superior propertiesfor use as agrochemical active ingredients (for example, greaterbiological activity, an advantageous spectrum of activity, an increasedsafety profile (including improved crop tolerance), improvedphysico-chemical properties, or increased biodegradability).

List of Abbreviations

° C.=degrees CelsiusCDCl₃=chloroform-dEDC=1-ethyl-3-(3-dimethylaminopropyl)carbodiimided=doubletm=multipletMHz=mega hertzmp=melting pointppm=parts per millions=singlett=triplet

EXAMPLES Example 1: This example illustrates the preparation of1-(1-phenylcyclopropyl)ethyl(2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate(Compound 1.a.006)

a) Preparation of N-methoxy-N-methyl-1-phenylcyclopropanecarboxamide

1,1′-Carbonyldiimidazole (2.5 g, 15 mmol) was added at room temperatureto a solution of 1-phenylcyclopropancarboxylic acid (1.6 g, 10 mmol) in20 ml of dichloroethane. The reaction mixture was heated to 60° C. for 4h, then N-methoxy-N-methyl-hydroxylamine (1.7 g, 15 mmol) was added andthe reaction mixture was stirred for 16 h at 60° C., then cooled to roomtemperature and diluted with water and dichloromethaner. The phases wereseparated and the aqueous phase was washed with dichloromethane. Thecombined organic layer was washed with water, dried over sodium sulfateand evaporated under reduced pressure, the remainder was purified bychromatography on silica gel, using ethyl acetate/cyclohexane as eluentsystem, to deliver N-methoxy-N-methyl-1-phenylcyclopropanecarboxamide(1.4 g, 6.7 mmol). ¹H-NMR (400 MHz, CDCl₃): δ=1.13 (t, 2H), 1.44 (t,2H), 3.12 (s, 3H), 3.20 (s, 3H), 7.20-7.36 (m, 5H).

b) Preparation of 1-(1-phenylcyclopropyl)ethanone

16 ml of a 1 M solution of methylmagnesium brmide in tetrhydrofuranewere added dropwise at 0° C. to a solution ofN-methoxy-N-methyl-1-phenylcyclopropanecarboxamide (1.4 g, 6.7 mmol) in16 ml of tetrahydrofuran. The reaction mixture was stirred for 16 h at50° C., then cooled to 0° C. and quenched by addition of saturatedaqueous ammoinium chloride solution. The mixture was diluted with ethylacetate, the phases were separated and the aqueous phase was washed withethyl acetate. The combined organic layer was washed with water, driedover sodium sulfate and evaporated under reduced pressure, the remainderwas purified by chromatography on silica gel, using ethylacetate/cyclohexane as eluent system, to deliver1-(1-phenylcyclopropyl)ethanone (0.9 g, 4.6 mmol)¹H-NMR (400 MHz,CDCl₃): δ=1.20 (t, 2H), 1.63 (t, 2H), 2.02 (s, 3H), 7.30-7.41 (m, 5H).

c) Preparation of 1-(1-phenylcyclopropyl)ethanol

Sodium borohydride (0.1 g, 2.7 mmol) was slowly added at 0° C. to asolution of 1-(1-phenylcyclopropyl)ethanone (0.9 g, 4.6 mmol) in 30 mlof methanol. The reaction mixture was stirred for 16 h at roomtemperature, then again cooled to 0° C. and quenched by addition ofsaturated aqueous ammonium chloride solution. The mixture was dilutedwith water and extracted with ethyl acetate. The organic layer waswashed with water and brine, dried over sodium sulfate and evaporatedunder reduced pressure. The residue was purified by chromatography onsilica gel, using ethyl acetate/heptane 1:3 as solvent system to deliver1-(1-phenylcyclopropyl)ethanol (0.56 g, 3.5 mmol). ¹H-NMR (400 MHz,CDCl₃): δ=0.77-0.90 (m, 4H), 1.15 (d, 3H), 3.41 (q, 1H), 7.25-7.41 (m,5H).

d) Preparation of 1-(1-phenylcyclopropyl)ethyl(2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate(Compound 1.a.006)

1-(1-phenylcyclopropyl)ethanol (0.28 g, 1.7 mmol), 4-pyrrolidinopyridine(0.26 g, 1.7 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide(EDC, 0.46 g, 2.9 mmol) were consecutively added at 0° C. to asuspension of(2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid(0.35 g, 1.5 mmol) in 18 ml of dichloromethane. The reaction mixture wasstirred for 5 h at room temperature, then quenched by addition ofdiluted hydrochloric acid and diluted with dichloromethane. The phaseswere separated, the organic layer was washed with saturated aqueoussodium bicarbonate solution and brine, dried over sodium sulfate andevaporated under reduced pressure. The residue was purified bychromatography on silica gel, using ethyl acetate/cyclohexane 1:3 assolvent system to deliver 1-(1-phenylcyclopropyl)ethyl(2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate(Compound 1.a.006, 0.15 g, 0.4 mmol)¹H-NMR (400 MHz, CDCl₃): δ=0.82-0.99(m, 4H), 1.21 (t, 3H), 1.52-1.61 (m, 3H), 3.97 (s, 3H), 4.63-4.77 (m,2H), 6.90 (d, 1H), 7.22-7.39 (m, 5H), 8.04 (d, 1H), 8.55 (bs, 1H), 12.21(s, 1H).

Throughout this description, temperatures are given in degrees Celsius(° C.) and “m.p.” means melting point. LC/MS means Liquid ChromatographyMass Spectrometry and the description of the apparatus and the methodis: (Method A: ACQUITY UPLC from Waters, Waters UPLC HSS T3, 1.8 μmparticle size, 30×2.1 mm column, 0.85 mL/min., 60° C., H₂O/MeOH95:5+0.05% HCOOH (90%)/CH₃CN+0.05% HCOOH (10%)—1.2 min.—CH₃CN+0.05%HCOOH (100%)—0.30 min., ACQUITY SQD Mass Spectrometer from Waters,ionization method: electrospray (ESI), Polarity: positive ions,Capillary (kV) 3.00, Cone (V) 30.00, Extractor (V) 2.00, SourceTemperature (° C.) 150, Desolvation Temperature (° C.) 350, Cone GasFlow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650). Method B: ACQUITY UPLCfrom Waters, Waters UPLC HSS T3, 1.8 μm particle size, 30×2.1 mm column,0.85 mL/min., 60° C., H₂O/MeOH 95:5+0.05% HCOOH (90%)/CH₃CN+0.05% HCOOH(10%)—2.7 min.—CH₃CN+0.05% HCOOH (100%)—0.30 min., ACQUITY SQD MassSpectrometer from Waters, ionization method: electrospray (ESI),Polarity: positive ions, Capillary (kV) 3.00, Cone (V) 30.00, Extractor(V) 2.00, Source Temperature (° C.) 150, Desolvation Temperature (° C.)350, Cone Gas Flow (L/Hr) 0, Desolvation Gas Flow (L/Hr) 650)).

TABLE 2 LC/MS data (Rt = Retention time) for selected compounds ofTable 1. Compound No. Compound name Structure LC/MS I.a.001(1,2-dimethyl-2-phenyl- propyl) (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate

(A) Rt = 1.09 min; MS: m/z = 387 (M + 1) I.a.0061-(1-phenylcyclopropyl)- ethyl (2S)-2-[(3-hydroxy- 4-methoxy-pyridine-2-carbonyl)amino]propanoate

(A) Rt = 1.07 min; MS: m/z = 385 (M + 1) I.a.010 1-(1,2-diphenylcyclo-propyl)ethyl (2S)-2-[(3- hydroxy-4-methoxy- pyridine-2-carbonyl)-amino]propanoate

(B) Rt = 1.92 min, 1.95 min, 1.97 min; MS: m/z = 461 [M + 1] I.a.0151-(1-phenylcyclohexyl)- ethyl (2S)-2-[(3-hydroxy- 4-methoxy-pyridine-2-carbonyl)amino]propanoate

(A) Rt = 1.21 min; MS: m/z = 427 (M + 1) I.d.006 1-[1-(3-bromophenyl)-cyclopropyl]ethyl (2S)- 2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate

(A) Rt = 1.15 min; MS: m/z = 463 (M + 1) I.j.001[2-(4-fluorophenyl)-1,2- dimethyl-propyl] (2S)-2- [(3-hydroxy-4-methoxy-pyridine-2-carbonyl)- amino]propanoate

(B) Rt = 1.75 min; MS: m/z = 405 (M + 1) I.j.010 1-[1-(4-fluorophenyl)-2-phenyl-cyclopropyl]- ethyl (2S)-2-[(3- hydroxy-4-methoxy-pyridine-2-carbonyl)- amino]propanoate

(B) Rt = 1.93 min, 1.97 min; MS: m/z = 479 (M + 1) I.j.0111-[1,2-bis(4-fluoro- phenyl)cyclopropyl]- ethyl (2S)-2-[(3-hydroxy-4-methoxy- pyridine-2-carbonyl)- amino]propanoate

(B) Rt = 1.95 min, 1.97 min; MS: m/z = 496 (M + 1) I.k.001[2-(4-chlorophenyl)- 1,2-dimethyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate

(B) Rt = 1.89 min; MS: m/z = 421 (M + 1) I.k.006 1-[1-(4-chlorophenyl)-cyclopropyl]ethyl (2S)- 2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate

(A) Rt = 1.12 min; MS: m/z = 419 (M + 1) I.k.012 1-[1-(4-chlorophenyl)-cyclobutyl]ethyl (2S)-2- ((3-hydroxy-4-methoxy- pyridine-2-carbonyl)-amino]propanoate

(A) Rt = 1.17 min; MS: m/z = 433 (M + 1) I.k.014 1-[1-(4-chlorophenyl)-cyclopentyl]ethyl (2S)- 2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate

(A) Rt = 1.22 min; MS: m/z = 447 (M + 1) I.k.015 1-[1-(4-chlorophenyl)-cyclohexyl]ethyl (2S)- 2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate

(A) Rt = 1.25 min; MS: m/z = 462 (M + 1) I.k.075 1-[1-(4-chlorophenyl)-cyclohexyl]ethyl (2S)-2- [(3-acetoxy-4-methoxy- pyridine-2-carbonyl)-amino]propanoate

(B) Rt = 2.13 min; MS: m/z = 503 (M + 1) I.m.001 [2-(4-bromophenyl)-1,2-dimethyl-propyl] (2S)-2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate

(A) Rt = 1.17 min; MS: m/z = 465 (M + 1) I.m.006 1-[1-(4-bromophenyl)-cyclopropyl]ethyl (2S)- 2-[(3-hydroxy-4- methoxy-pyridine-2-carbonyl)amino]propanoate

(B) Rt = 1.88 min; MS: m/z = 463 (M + 1), 465 (M + 3) I.m.0121-[1-(4-bromophenyl)- cyclobutyl]ethyl (2S)- 2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate

(A) Rt = 1.20 min; MS: m/z = 477 (M + 1) I.o.0141-[1-[4-(trifluoromethyl)- phenyl]cyclopentyl]ethyl(2S)-2-[(3-hydroxy-4- methoxy-pyridine-2- carbonyl)amino]prapanoate

(B) Rt = 2.08 min; MS: m/z = 481 (M + 1) I.q.006 1-[1-[4-(trifluoro-methoxy)phenyl]cyclo- propyl]ethyl (2S)-2- [(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate

(B) Rt = 1.95 min; MS: m/z = 470 (M +1) I.t.006 1-[1-(3,4-dichloro-phenyl)cyclopropyl]- ethyl (2S)-2-[(3- hydroxy-4-methoxy-pyridine-2-carbonyl)- amino]propanoate

(B) Rt = 1.96 min; MS: m/z = 453 (M + 1) I.u.007 1-[1-(4-ethoxyphenyl)-2,2-difluorocyclopropyl]- ethyl (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2- carbonyl)amino]propanoate

(B) Rt = 1.69 min; MS: m/z = 466 (M + 1) I.v.006 1-[1-(1-naphthyl)cyclo-propyl]ethyl (2S)-2-[(3- hydroxy-4-methoxy- pyridine-2-carbonyl)-amino]propanoate

(B) Rt = 1.90 min; MS: m/z = 435 (M + 1) I.v.010 1-[1-(1-naphthyl)-2-phenyl-cyclopropyl]- ethyl (2S)-2-[(3- hydroxy-4-methoxy-pyridine-2-carbonyl)- amino]propanoate

(B) Rt = 2.06 min, 2.09 min, 2.11 min; MS: m/z = 511 (M + 1) I.v.0111-[2-(4-fluorophenyl)- 1-(1-naphthyl)cyclo- propyl]ethyl (2S)-2-[(3-hydroxy-4- methoxy-pyridine-2- carbonyl)amino]- propanoate

(B) Rt = 2.08 min, 2.10 min, 2.11 min; MS: m/z = 529 (M + 1) I.v.0661-[1-(1-naphthyl)cyclo- propyl]ethyl (2S)-2-[(3- acetoxy-4-methoxy-pyridine-2-carbonyl)- amino]propanoate

(B) Rt = 1.92 min; MS: m/z = 477 (M + 1) I.ah.001 [2-(2,5-difluoro-phenyl)-1,2-dimethyl- propyl] (2S)-2-[(3- hydroxy-4-methoxy-pyridine-2-carbonyl)- amino]propanoate

(B) Rt = 1.76 min; MS: m/z = 424 (M + 1)

BIOLOGICAL EXAMPLES

Blumeria graminis f. sp. tritici (Erysiphe raminis f. sp.tritici)/wheat/leaf disc preventative (Powdery Mildew on Wheat)

Wheat leaf segments cv. Kanzler are placed on agar in a multiwell plate(24-well format) and sprayed with the test compound formulated with DMSOand Tween20 and diluted in water. The leaf disks are inoculated byshaking powdery mildew infected plants above the test plates 1 day afterapplication. The inoculated leaf disks are incubated at 20° C. and 60%rh under a light regime of 24 h darkness followed by 12 h light/12 hdarkness in a climate chamber and the activity of a compound is assessedas percent disease control compared to untreated when an appropriatelevel of disease damage appears on untreated check leaf segments (6-8days after application).

Compounds I.k.012, I.k.015 and I.m.012 at 200 ppm in the formulationgive at least 80% disease control in this test when compared tountreated control leaf disks under the same conditions, which showextensive disease development.

Botryotinia fuckeliana (Botrytis cinerea)/Liquid Culture (Gray Mould)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (Vogels broth). After placing a (DMSO) solution of testcompound into a microtiter plate (96-well format), the nutrient brothcontaining the fungal spores is added. The test plates are incubated at24° C. and the inhibition of growth is determined photometrically 3-4days after application.

Compounds I.a.001, I.a.006, I.a.010, I.a.015, I.d.006, I.j.001, I.k.006,I.k.012 I.k.014, I.k.015, I.m.001, I.m.012, I.q.006, I.t.006, I.u.007,and I.v.066 at 200 ppm in the formulation give at least 80% diseasecontrol in this test when compared to untreated control leaf disks underthe same conditions, which show extensive disease development.

Glomerella lacenarium (Colletotrichum lacenarium)/Liquid Culture(Anthracnose)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is measuredphotometrically 3-4 days after application.

Compounds I.a.010, I.a.015, I.d.006, I.j.001, I.j.010, I.j.011, I.k.012,I.k.014, I.k.015, I.k.075, I.m.001, I.m.012, I.q.006, I.t.006, I.u.007,I.v.006, I.v.010, I.v.011, I.v.066 and I.ah.001 at 200 ppm in theformulation give at least 80% disease control in this test when comparedto untreated control leaf disks under the same conditions, which showextensive disease development.

Magnaporthe risea (Pyricularia Oryzae)/Rice/Leaf Disc Preventative (RiceBlast)

Rice leaf segments cv. Ballila are placed on agar in a multiwell plate(24-well format) and sprayed with the test compound formulated with DMSOand Tween20 and diluted in water. The leaf segments are inoculated witha spore suspension of the fungus 2 days after application. Theinoculated leaf segments are incubated at 22° C. and 80% rh under alight regime of 24 h darkness followed by 12 h light/12 h darkness in aclimate cabinet and the activity of a compound is assessed as percentdisease control compared to untreated when an appropriate level ofdisease damage appears in untreated check leaf segments (5-7 days afterapplication).

Compounds I.a.006, I.a.010, I.a.015, I.k.012, I.k.014, I.k.075, I.m.001,I.m.012, I.q.006, I.t.006, I.u.007, I.v.066 and I.ah.001 at 200 ppm inthe formulation give at least 80% disease control in this test whencompared to untreated control leaf disks under the same conditions,which show extensive disease development

Monocraphella nivalis (Microdochium nivale)/Liquid Culture (Foot RotCereals)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is determinedphotometrically 4-5 days after application.

Compounds I.a.001, I.a.006 I.k.006, I.a.010, I.a.015, I.d.006, I.j.001,I.j.011, I.k.012 I.k.014, I.k.015, I.m.001, I.m.012, I.q.006, I.t.006,I.u.007, I.v.006, I.v.066 and I.ah.001 at 200 ppm in the formulationgive at least 80% disease control in this test when compared tountreated control leaf disks under the same conditions, which showextensive disease development.

Mycosphaerella arachidis (Cercospora arachidicola)/Liquid Culture (EarlyLeaf Spot)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is determinedphotometrically 4-5 days after application.

Compounds I.a.001, I.a.006, I.k.006, I.a.010, I.a.015, I.d.006, I.j.001,I.j.010, I.j.011, I.k.012, I.k.014, I.k.015, I.k.075, I.m.001, I.m.012,I.q.006, I.t.006, I.v.006, I.v.010, I.v.011, I.v.066 and I.ah.001 at 200ppm in the formulation give at least 80% disease control in this testwhen compared to untreated control leaf disks under the same conditions,which show extensive disease development.

Mycosphaerella Raminicola (Septoria tritici)/Liquid Culture (SeptoriaBlotch)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is determinedphotometrically 4 to 5 days after application.

Compounds I.a.001, I.a.006, I.a.010, I.a.015, I.d.006, I.j.001, I.j.010,I.j.011, I.k.006, I.k.012, I.k.014, I.k.015, I.k.075, I.m.001, I.m.012,I.q.006, I.t.006, I.u.007, I.v.006, I.v.010, I.v.011, I.v.066 andI.ah.001 at 200 ppm in the formulation give at least 80% disease controlin this test when compared to untreated control leaf disks under thesame conditions, which show extensive disease development.

Phaeosphaeria Nodorum (Septoria nodorum)/Wheat/Leaf Disc Preventative(Glume Blotch)

Wheat leaf segments cv. Kanzler are placed on agar in a multiwell plate(24-well format) and sprayed with the formulated test compound dilutedin water. The leaf disks are inoculated with a spore suspension of thefungus 2 days after application. The inoculated test leaf disks areincubated at 20° C. and 75% rh under a light regime of 12 h light/12 hdarkness in a climate cabinet and the activity of a compound is assessedas percent disease control compared to untreated when an appropriatelevel of disease damage appears in untreated check leaf disks (5-7 daysafter application).

Compound I.a.001, I.a.010, I.a.015, I.k.006, I.k.012, I.k.015, I.k.075,I.m.001, I.v.006, I.v.066 and I.ah.001 at 200 ppm in the formulationgive at least 80% disease control in this test when compared tountreated control leaf disks under the same conditions, which showextensive disease development.

Puccinia recondita f. Sp. Tritici/Wheat/Leaf Disc Preventative (BrownRust)

Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates(24-well format) and sprayed with the formulated test compound dilutedin water. The leaf disks are inoculated with a spore suspension of thefungus 1 day after application. The inoculated leaf segments areincubated at 19° C. and 75% rh under a light regime of 12 h light/12 hdarkness in a climate cabinet and the activity of a compound is assessedas percent disease control compared to untreated when an appropriatelevel of disease damage appears in untreated check leaf segments (7-9days after application).

Compound I.a.001, I.a.006, I.a.010, I.a.015, I.d.006, I.j.001, I.j.010,I.j.011, I.k.006, I.k.012, I.k.014, I.k.015, I.k.075, I.m.001, I.m.012,I.q.006, I.t.006, I.u.007, I.v.006, I.v.010, I.v.011, I.v.066 andI.ah.001 at 200 ppm in the formulation give at least 80% disease controlin this test when compared to untreated control leaf disks under thesame conditions, which show extensive disease development.

What is claimed is:
 1. A compound of formula (I):

wherein, R¹ is C₁-C₁₂alkyl or C₁-C₆haloalkyl; R² is hydroxy,C₂-C₆acyloxy, C₂-C₆haloacyloxy, C₁-C₆alkoxyC₁-C₆alkoxy,C₁-C₆haloalkoxyC₁-C₆alkoxy, C₁-C₆alkoxyC₁-C₆haloalkoxy,C₂-C₆acyloxyC₁-C₆alkoxy, C₂-C₆haloacyloxyC₁-C₆alkoxy orC₂-C₆acyloxyC₁-C₆haloalkoxy; R³ is hydrogen, C₁-C₆alkyl, C₁-C₆alkoxy orC₃-C₈cycloalkyl; R⁴ and R⁵ are independently C₁-C₁₂alkyl,C₃-C₈cycloalkyl, C₁-C₆haloalkyl, C₁-C₆alkoxyC₁-C₆alkyl orC₃-C₈halocycloalkyl; R⁶ and R⁷ are independently C₁-C₆alkyl orC₃-C₈cycloalkyl; or R⁶ and R⁷ together with the carbon atom to whichthey are attached form a C₃-C₈cycloalkyl ring which is optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁹, or is optionally substituted by a singlesubstituent which is R¹⁰, or is optionally substituted by 1 or 2substituents, which may be the same or different, selected from R⁹ and asingle substituent which is R¹⁰; R⁸ is phenyl, phenoxy, naphthyl,naphthyloxy, heteroaryl or heteroaryloxy, wherein the heteroaryl moietyis a 5- or 6-membered aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterodiaryl orheterodiaryloxy, wherein the heterodiaryl moiety is a 9- or 10-memberedbicyclic aromatic system which comprises 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S, wherein each phenyl, naphthyl,heteroaryl or heterodiaryl is optionally substituted by 1, 2 or 3substituents, which may be the same or different, selected from R⁹; R⁹is halogen, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy; and R¹⁰ is phenyl or cyclopropyl each optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from fluoro, chloro, bromo, cyano, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy; or a salt or an N-oxide thereof.
 2. The compoundaccording to claim 1, wherein R¹ is methyl or ethyl.
 3. The compoundaccording to claim 1, wherein R² is hydroxy, acetoxy, propanoyloxy,acetoxymethoxy, propanoyloxymethoxy, 2-methyl-prop anoyloxymethoxy. 4.The compound according to claim 1, wherein R² is hydroxy.
 5. Thecompound according to claim 1, wherein R³ is hydrogen.
 6. The compoundaccording to claim 1, wherein R⁴ is methyl or ethyl and R⁵ is methyl orethyl.
 7. The compound according to claim 1, wherein R⁶ and R⁷ areindependently C₁-C₄alkyl, and preferably methyl.
 8. The compoundaccording to claim 1, wherein R⁶ and R⁷ together with the carbon atom towhich they are attached form a C₃-C₆cycloalkyl ring which is optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁹, or is optionally substituted by a singlesubstituent which is R¹⁰, or is optionally substituted by 1 or 2substituents, which may be the same or different, selected from R⁹ and asingle substituent which is R¹⁰.
 9. The compound according to claim 1,wherein R⁸ is phenyl, naphthyl, furyl, benzofuryl, thienyl,benzothienyl, pyrrolyl, indolyl, pyrazolyl, indazolyl, imidazolyl,benzimidazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl,pyridyl, quinolinyl, isoquinolinyl, pyridazinyl, cinnolinyl,pyrimidinyl, quinazolinyl, pyrazinyl, phenoxy, naphthyloxy, pyridyloxyor quinolinyloxy, optionally substituted by 1, 2 or 3 substituents,which may be the same or different, selected from R⁹.
 10. The compoundaccording to claim 1, wherein R⁸ is phenyl, naphthyl, thienyl, indolyl,pyridyl, quinolinyl, pyridazinyl, pyrimidinyl, pyrazinyl, phenoxy,pyridyloxy or quinolinyloxy optionally substituted by 1 or 2substituents, which may be the same or different, selected from R⁹. 11.The compound according to claim 1, wherein R⁸ is phenyl, thienyl,pyridyl, phenoxy or pyridyloxy optionally substituted by a singlesubstituent selected from R⁹.
 12. An agrochemical composition comprisinga fungicidally effective amount of a compound of formula (I) accordingto claim
 1. 13. The composition according to claim 12, furthercomprising at least one additional active ingredient and/or anagrochemically-acceptable diluent or carrier.
 14. A method ofcontrolling or preventing infestation of useful plants byphytopathogenic microorganisms, wherein a fungicidally effective amountof a compound of formula (I) according to claim 1, or a compositioncomprising this compound as active ingredient, is applied to the plants,to parts thereof or the locus thereof.
 15. Use of a compound of formula(I) according to claim 1 as a fungicide.